Combinations of herbicides and safeners

ABSTRACT

This invention provides for, inter alia, a herbicidal composition comprising a mixture of:  
     A. a herbicidally effective amount of at least one compound of the formula  
                 
 
     where V and Z are defined in the specification; and  
     B. an antidote.

DESCRIPTION

[0001] The invention relates to the technical field of the cropprotection products, in particular herbicide/antidote combinations(active substance/safener combinations) which are outstandingly suitablefor the use against competing harmful plants in crops of useful plants.

[0002] Some of the more recent herbicidal active substances whichinhibit p-hydroxyphenylpyruvate dioxygenase (HPPDO) have very good usecharacteristics and can be employed at very low application ratesagainst a broad spectrum of grass weeds and broad-leaved weeds (see, forexample, M. P. Prisbylla et al., Brighton Crop ProtectionConference—Weeds (1993), 731-738).

[0003] However, many of these highly efficient active substances are notfully compatible with (i.e. not sufficiently selective in) someimportant crop plants such as maize, rice or cereals, so that their useis strictly limited. In certain crops, they can therefore not beemployed, or at such low application rates that the desired broadherbicidal efficacy towards harmful plants is not guaranteed.Specifically, many of the abovementioned herbicides cannot be employedfully selectively against harmful plants in maize, rice, cereals or someother crops.

[0004] To overcome these disadvantages, it is known to employ herbicidalactive substances in combination with a so-called safener or antidote. Asafener for the purpose of the invention is a compound or a mixture ofcompounds which compensates for, or reduces, the phytotoxic propertiesof a herbicide towards useful plants without substantially reducing theherbicidal action against harmful plants.

[0005] The identification of a safener for a particular class ofherbicides remains a difficult task since the exact mechanisms by whicha safener reduces the harmful effect of herbicides are unknown. The factthat a compound in combination with a particular herbicide acts as asafener allows no conclusions as to whether such a compound also acts asa safener with other classes of herbicide. Thus, it has emerged that,when using safeners for protecting the useful plants from herbicidedamage, the safeners may still have a number of disadvantages in manycases. These are:

[0006] the safener reduces the action of the herbicides against theharmful plants,

[0007] the useful-plant-protecting properties are insufficient,

[0008] in combination with a given herbicide, the spectrum of the usefulplants in which the safener/herbicide is to be used is insufficientlywide,

[0009] a given safener may not be combined with a sufficiently largenumber of herbicides.

[0010] It was an object of the present invention to identify compoundswhich, in combination with the abovementioned herbicides are suitablefor increasing the selectivity of these herbicides towards importantcrop plants.

[0011] Surprisingly, a group of compounds has now been found which,together with specific herbicides which act as HPPDO inhibitors,increase the selectivity of these herbicides towards important cropplants.

[0012] The invention therefore relates to a herbicidally activecomposition comprising a mixture of

[0013] A. a herbicidally active amount of one or more compounds of theformula (I)

[0014]  in which

[0015] V is a radical selected from the group consisting of (V1) to(V4),

[0016]  where the symbols and indices have the following meanings:

[0017] R is hydrogen, (C₁-C₄)alkoxycarbonyl, (C₁-C₄)haloalkoxycarbonyl,COOH, cyano, preferably hydrogen, (C₁-C₄)alkoxycarbonyl;

[0018] R¹ is hydrogen or a (C₁-C₇)carbon-containing radical such as(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C₇)cycloalkyl,(C₃-C₇)cycloalkenyl, (C₁-C₄)alkyl-(C₃-C₇)cycloalkyl,(C₃-C₇)halocycloalkyl, (C₁-C₄)alkylthiocycloalkyl, (C₁-C₄)haloalkyl,(C₂-C₄)haloalkenyl, preferably (C₃-C₇)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₇)cycloalkyl;

[0019] R² is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,halogen, (C₁-C₄)haloalkoxy, cyano, nitro, preferably hydrogen;

[0020] R³ is hydrogen or a (C₁-C₄)carbon-containing radical such as(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)halo-alkylsulfonyl, arylsulfonyl, arylcarbonyl-(C₁-C₄)alkyl,aryl-(C₁-C₄)alkyl, preferably hydrogen, (C₁-C₄) alkyl, arylsulfonyl,benzyl;

[0021] R⁴ is hydrogen or a (C₁-C₇)carbon-containing radical such as(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl, phenyl,benzyl, preferably (C₁-C₄)alkyl;

[0022] R⁵ is a (C₁-C₁₂)carbon-containing radical such as (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)dialkoxy-(C₁-C₄)alkyl,(C₁-C₄)alkylthio, halogen, substituted or unsubstituted aryl,tetrahydropyran-4-yl, tetrahydropyran-3-yl, tetrahydrothiopyran-3-yl,1-methylthio-cyclopropyl, 2-ethylthiopropyl, preferably (C₁-C₄)alkyl,(C₁-C₄)alkoxy;

[0023] R⁶ is hydroxyl or a (C₁-C₄)carbon-containing radical such as(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, formyloxy, (C₁-C₄)alkylcarbonyloxy,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, preferably hydroxyl,(C₁-C₄)alkoxy;

[0024] R⁷ is a (C₁-C₇)carbon-containing radical such as (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₃-C₇)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₇)cycloalkyl,(C₃-C₇)halocycloalkyl, preferably (C₃-C₇)cycloalkyl;

[0025] R⁸ is cyano or a (C₁-C₄)carbon-containing radical such as(C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylthio, (C₁-C₄)alkylaminocarbonyl,(C₁-C₄)dialkylaminocarbonyl, preferably cyano;

[0026] m is an integer from 0 to 6, preferably 0 to 3,

[0027] and Z is a radical selected from the group consisting of (Z1) to(Z4),

[0028]  where the symbols and indices have the following meanings:

[0029] R⁹ is nitro, amino, halogen or a (C₁-C₈)carbon-containing radicalsuch as (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,(C₂-C₄)haloalkenyl, (C₂-C₄)haloalkynyl, (C₁-C₄)haloalkoxy,(C₁-C₄)haloalkylthio, (C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylthio, arylsulfonyl, arylsulfinyl,arylthio, (C₁-C₄)alkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylaminosulfonyl,(C₁-C₄)dialkylaminosulfonyl, (C₁-C₄)alkylcarbamoyl,(C₁-C₄)dialkylcarbamoyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, phenoxy, cyano,aryl, alkylamino, dialkylamino, preferably (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkoxycarbonyl;

[0030] R¹⁰ is substituted or unsubstituted benzyl, substituted orunsubstituted heteroaryl, heterocyclyl, preferably furanyl, thiazolyl,triazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolinyl, morpholino,and imidazolyl; heteroaryl-(C₁-C₄)alkyl, preferably triazolylmethyl,pyrazolylmethyl, thiazolylmethyl, di-(C₁-C₄)alkylphosphono-(C₁-C₄)alkyl,preferably diethylphosphonomethyl, dimethylphosphonomethyl or SF₅;

[0031] R¹¹ is identical or different hydrogen, (C₁-C₄)alkyl, halogen,preferably (C₁-C₄)alkyl;

[0032] R¹² is identical or different (C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, halogen, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)haloalkynyl, (C₁-C₄)haloalkoxy, (C₁-C₄)haloalkylthio,(C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylthio,(C₁-C₄)alkoxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylaminosulfonyl,(C₁-C₄)dialkylaminosulfonyl, (C₁-C₄)alkylcarbamoyl,(C₁-C₄)dialkylcarbamoyl, (C₁-C₄)alkoxyalkyl, phenoxy, nitro, cyano,aryl, di-(C₁-C₄)alkylphosphono-(C₁-C₄)alkyl, preferably (C₁-C₄)alkyl,halogen, (C₁-C₄)haloalkyl, (C₁-C₄)alkylsulfonyl, (C₁-C₄)alkoxycarbonyl;

[0033] q is 0, 1, 2, 3 or 4;

[0034] r is 0, 1, 2 or 3;

[0035] t is 1 or 2;

[0036] u is 0, 1 or 2;

[0037] v is 1 or 2;

[0038] X¹ is O, CR¹⁴R¹⁵, CHOH, C═O, C═NO(C₁-C₄)alkyl;

[0039] X² is O, S, SO, SO₂, CH₂, NH, N(C₁-C₄)alkyl, NSO₂(C₁-C₄)alkyl,preferably SO₂;

[0040] U¹ together with the linked carbon atoms forms a carbocyclic orheterocyclic ring which can be aromatic or fully or partially saturated,preferably a pyrazole, imidazole, pyrrole, pyridine, pyrimidine,thiazole, thienyl, oxazole or furan ring;

[0041] U² is O, S, SO, SO₂, CH₂, NH, N(C₁-C₄)alkyl, NSO₂(C₁-C₄)alkyl,preferably SO₂;

[0042] R¹³ is hydrogen, (C₁-C₄)alkyl, (C₃-C₇)cycloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, optionally substituted phenyl, optionally substitutedbenzyl, (C₁-C₄)acyl;

[0043] R¹⁴, R¹⁵ is identical or different hydrogen, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthioor R¹⁴ and R¹⁵ together form one of the groups —O—(CH₂)₂—O—,—O—(CH₂)₃—O—, S—(CH₂)₂—S—, —S—(CH₂)₃—S—, —(CH₂)₄—, —(CH₂)₅—;

[0044] R¹⁶ is (C₁-C₂)alkyl;

[0045] Y¹, Y² are SO₂ or CO, with the proviso that Y¹≠Y²,

[0046] and

[0047] B. an antidote-effective amount of one or more compounds selectedfrom the groups consisting of a) to e):

[0048] a) compounds of the formulae (II) to (IV),

[0049]  where the symbols and indices having the following meanings:

[0050] n′ is a natural number from 1 to 5, preferably 1 to 3;

[0051] T is a (C₁ or C₂)-alkanediyl chain which is unsubstituted orsubstituted by one or two (C₁-C₄)alkyl radicals or by[(C₁-C₃)-alkoxy]carbonyl;

[0052] W is an unsubstituted or substituted divalent heterocyclicradical selected from the group consisting of the partially unsaturatedor aromatic five-ringed heterocycles having 1 to 3 hetero ring atoms ofthe type N or O, the ring containing at least one nitrogen atom and notmore than one oxygen atom, preferably a radical selected from the groupconsisting of (W1) to (W4),

[0053] m′ is 0 or 1;

[0054] R¹⁷, R¹⁹ are identical or different hydrogen, halogen,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, nitro or (C₁-C₄)haloalkyl;

[0055] R¹⁸, R²⁰ are identical or different OR²⁴, SR²⁴ or NR²⁴R²⁵ or asaturated or unsaturated 3- to 7-membered heterocycle having at leastone nitrogen atom and up to 3 hetero atoms which is linked to thecarbonyl group in (II) or (III) via the nitrogen atom and which isunsubstituted or substituted by radicals selected from the groupconsisting of (C₁-C₄)alkyl, (C₁-C₄)alkoxy or optionally substitutedphenyl, preferably a radical of the formula OR²⁴, NHR²⁵ or N(CH₃)₂, inparticular of the formula OR²⁴;

[0056] R²⁴ is hydrogen or an unsubstituted or substituted aliphatichydrocarbon radical, preferably having in total 1 to 18 carbon atoms;

[0057] R²⁵ is hydrogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy or substituted orunsubstituted phenyl;

[0058] R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₁₂)cycloalkyl ortri-(C₁-C₄)-alkylsilyl;

[0059] R²⁷, R²⁸, R²⁹ are identical or different hydrogen, (C₁-C₈)alkyl,(C₁-C₈)haloalkyl, (C₃-C₁₂)cycloalkyl or substituted or unsubstitutedphenyl;

[0060] R²¹ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₃-C₇)cycloalkyl, preferably dichloromethyl;

[0061] R²², R²³ is identical or different hydrogen, (C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl,(C₁-C₄)alkylcarbamoyl-(C₁-C₄)alkyl,(C₂-C₄)alkenylcarbamoyl-(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,dioxolanyl-(C₁-C₄)alkyl, thiazolyl, furyl, furylalkyl, thienyl,piperidyl, substituted or unsubstituted phenyl, or R²² and R²³ togetherform a substituted or unsubstituted heterocyclic ring, preferably anoxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidineor benzoxazine ring;

[0062] or

[0063] b) one or more compounds from the group consisting of:

[0064] 1,8-naphthalic anhydride,

[0065] methyl diphenylmethoxyacetate,

[0066] cyanomethoxyimino(phenyl)acetonitrile (cyometrinil),

[0067] 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil),

[0068] 4′-chloro-2,2,2-trifluoroacetophenoneO-1,3-dioxolan-2-ylmethyloxime (fluxofenim),

[0069] 4,6-dichloro-2-phenylpyrimidine (fenclorim),

[0070] benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate(flurazole),

[0071] 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),

[0072] N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron),

[0073] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0074] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0075] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,

[0076] 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0077] (2,4-dichlorophenoxy)acetic acid (2,4-D),

[0078] (4-chlorophenoxy)acetic acid,

[0079] (R,S)-2-(4chloro-o-tolyloxy)propionic acid (mecoprop),

[0080] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

[0081] (4-chloro-o-tolyloxy)acetic acid (MCPA),

[0082] 4-(4-chloro-o-tolyloxy)butyric acid,

[0083] 4-(4-chlorophenoxy)butyric acid,

[0084] 3,6-dichloro-2-methoxybenzoic acid (dicamba),

[0085] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate(lactidichlor)

[0086] and their salts and esters, preferably (C₁-C₈);

[0087] c) N-acylsulfonamides of the formula (V) and their salts,

[0088]  where

[0089] R³⁰ is hydrogen, a carbon-containing radical such as ahydrocarbon radical, a hydrocarbon oxy radical, a hydrocarbon thioradical or a heterocyclyl radical, each of the last-mentioned 4 radicalsbeing unsubstituted or substituted by one or more identical or differentradicals selected from the group consisting of halogen, cyano, nitro,amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicalsof the formula —Z^(a)—R^(a), each hydrocarbon moiety preferably having 1to 20 carbon atoms and a carbon-containing radical R³⁰ inclusive ofsubstituents preferably having 1 to 30 carbon atoms;

[0090] R³¹ is hydrogen or (C₁-C₄)alkyl, preferably hydrogen, or

[0091] R³⁰ and R³¹ together with the group of the formula —CO—N— are theradical of a 3- to 8-membered saturated or unsaturated ring;

[0092] R³² is identical or different halogen, cyano, nitro, amino,hydroxyl, carboxyl, formyl, CONH₂, SO₂NH₂ or a radical of the formula—Z^(b)—R^(b);

[0093] R³³ is hydrogen or (C₁-C₄)alkyl, preferably H;

[0094] R³⁴ is identical or different halogen, cyano, nitro, amino,hydroxyl, carboxyl, CHO, CONH₂, SO₂NH₂ or a radical of the formula—Z^(c)—R^(c);

[0095] R^(a) is a hydrocarbon radical or a heterocyclyl radical, each ofthe two last-mentioned radicals being unsubstituted or substituted byone or more identical or different radicals selected from the groupconsisting of halogen, cyano, nitro, amino, hydroxyl, mono- anddi-[(C₁-C₄)alkyl]amino, or is an alkyl radical in which more than one,preferably 2 or 3, nonadjacent CH₂ groups are each replaced by an oxygenatom;

[0096] R^(b),R^(c) identical or different are a hydrocarbon radical or aheterocyclyl radical, each of the two last-mentioned radicals beingunsubstituted or substituted by one or more identical or differentradicals selected from the group consisting of halogen, cyano, nitro,amino, hydroxyl, phosphoryl, halo(C₁-C₄)alkoxy, mono- anddi[(C₁-C₄)alkyl]amino, or are an alkyl radical in which more than one,preferably 2 or 3, nonadjacent CH₂ groups are each replaced by an oxygenatom;

[0097] Z^(a) is a divalent group of the formula —O—, —S—, —CO—, —CS—,—CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—, —CO—NR*—, —NR*—CO—,—SO₂—NR*— or —NR*—SO₂—, the bond shown on the right of the divalentgroup in question being the bond to the radical R^(a) and the R* in thelast-mentioned 5 radicals independently of one another being in eachcase H, (C₁-C₄)alkyl or halo(C₁-C₄)alkyl;

[0098] Z^(b),Z^(c) independently of one another are a direct bond or adivalent group of the formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—,—O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—, —SO₂—NR*—, —NR*—SO₂—, —CO—NR*— or—NR*—CO—, the bond shown on the right of the divalent group in questionbeing the bond to the radical R^(b) or R^(c), respectively, and the R*in the last-mentioned 5 radicals independently of one another being ineach case H, (C₁-C₄)alkyl or halo(C₁-C₄)alkyl;

[0099] n is an integer from 0 to 4, preferably 0, 1 or 2, in particular0 or 1, and

[0100] m is an integer from 0 to 5, preferably 0, 1, 2 or 3, inparticular 0, 1 or 2.

[0101] d) Acylsulfamoylbenzamides of the formula (VI), if appropriate insalt form,

[0102]  where

[0103] X³ is CH or N;

[0104] R³⁵ is hydrogen, heterocyclyl or a hydrocarbon radical, the twolast-mentioned radicals optionally being substituted by one or more,identical or different radicals selected from the group consisting ofhalogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH₂, SO₂NH₂ andZ^(a)—R^(a);

[0105] R³⁶ is hydrogen, hydroxyl, (C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy, the fivelast-mentioned radicals optionally being substituted by one or moreidentical or different radicals selected from the group consisting ofhalogen, hydroxyl, (C₁-C₄)alkyl, (C₁-C₄)alkoxy and (C₁-C₄)alkylthio, or

[0106] R³⁵ and R³⁶ together with the nitrogen atom to which they areattached are a 3- to 8-membered saturated or unsaturated ring;

[0107] R³⁷ is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO,CONH₂, SO₂NH₂ or Z^(b)—R^(b);

[0108] R³⁸ is hydrogen, (C₁-C₄)alkyl, (C₂-C₄)alkenyl or (C₂-C₄)alkynyl;

[0109] R³⁹ is halogen, cyano, nitro, amino, hydroxyl, carboxyl,phosphoryl, CHO, CONH₂, SO₂NH₂ or Z^(c)—R^(c);

[0110] R^(a) is a (C₂-C₂₀)alkyl radical whose carbon chain isinterrupted once or more by oxygen atoms, or is heterocyclyl or ahydrocarbon radical, the two last-mentioned radicals optionally beingsubstituted by one or more, identical or different radicals selectedfrom the group consisting of halogen, cyano, nitro, amino, hydroxyl,mono- and di[(C₁-C₄)alkyl]amino;

[0111] R^(b), R^(c) identical or different are a (C₂-C₂₀)alkyl radicalwhose carbon chain is interrupted once or more by oxygen atoms, or areheterocyclyl or a hydrocarbon radical, the two last-mentioned radicalsoptionally being substituted by one or more, identical or differentradicals selected from the group consisting of halogen, cyano, nitro,amino, hydroxyl, phosphoryl, (C₁-C₄)haloalkoxy, mono- anddi[(C₁-C₄)-alkyl]amino;

[0112] Z^(a) is a divalent unit selected from the group consisting of O,S, CO, CS, C(O)O, C(O)S, SO, SO₂, NR^(d), C(O)NR^(d) or SO₂NR^(d);

[0113] Z^(b), Z^(c) identical or different are a direct bond or adivalent unit selected from the group consisting of O, S, CO, CS, C(O)O,C(O)S, SO, SO₂, NR^(d), SO₂NR^(d) or C(O)NR^(d);

[0114] R^(d) is hydrogen, (C₁-C₄)alkyl or (C₁-C₄)haloalkyl;

[0115] n is an integer from 0 to 4, and

[0116] m in the event that X is CH, is an integer from 0 to 5 and, inthe event that X is N, an integer from 0 to 4;

[0117] e) compounds of the formula (VII),

[0118]  where the symbols and indices have the following meanings:

[0119] R⁴⁰ is H, (C₁-C₄)alkyl, (C₁-C₄)alkyl substituted by(C₁-C₄)alkyl-X⁴ or (C₁-C₄)haloalkyl-X⁴, (C₁-C₄)haloalkyl, NO₂, CN,—COO—R⁴³, NR₂ ⁴⁴, SO₂NR₂ ⁴⁵ or CONR₂ ⁴⁶;

[0120] R⁴¹ is H, halogen, (C₁-C₄)alkyl, CF₃, (C₁-C₄)alkoxy or(C₁-C₄)haloalkoxy;

[0121] R⁴² is H, halogen or (C₁-C₄)alkyl;

[0122] Q¹, Q², E, G are identical or different, —O—, —S—, —CR₂ ⁴⁷—,—CO—, NR⁴⁸— or a group of the formula (VIII),

[0123] with the proviso that

[0124] a) at least one of the groups Q¹, Q², E, G is a carbonyl group,that exactly one of this group is a radical of the formula (VIII) andthat the group of the formula (VIII) is adjacent to a carbonyl group,and

[0125] b) two adjacent groups Q¹, Q², E and G cannot simultaneously beoxygen;

[0126] R^(a) is identical or different H or (C₁-C₈)alkyl or the tworadicals R^(a) together are (C₂-C₆)alkylene;

[0127] A is R^(b)—Y³— or —NR₂ ⁴⁹;

[0128] X⁴ is —O— or —S(O)_(p)—;

[0129] Y³ is —O— or —S—;

[0130] R^(b) is H, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy(C₁-C₈)alkyl, (C₃-C₆)alkenyloxy(C₁-C₈)alkyl, orphenyl(C₁-C₈)alkyl, the phenyl ring optionally being substituted byhalogen, (C₁-C₄)alkyl, CF₃, methoxy or methyl-S(O)_(p); (C₃-C₆)alkenyl,(C₃-C₆)haloalkenyl, phenyl(C₃-C₆)alkenyl, (C₃-C₆)alkynyl,phenyl(C₃-C₆)alkynyl, oxetanyl, furfuryl, tetrahydrofuryl;

[0131] R⁴³ is H or (C₁-C₄)alkyl;

[0132] R⁴⁴ is identical or different H, (C₁-C₄)alkyl,(C₁-C₄)alkylcarbonyl or the two radicals R⁴⁴ together are(C₄-C₅)alkylene;

[0133] R⁴⁵, R⁴⁶ are independently of one another in each case identicalor different H, (C₁-C₄)alkyl, or the two radicals R⁴⁵ and/or R⁴⁶together are (C₄-C₅)alkylene, it being possible for one CH₂ group to bereplaced by O or S or by one or two CH₂ groups to be replaced by—NR^(c)—;

[0134] R^(c) is H or (C₁-C₈)alkyl;

[0135] R⁴⁷ is identical or different H, (C₁-C₈)alkyl or the two radicalsR⁴⁷ together are (C₂-C₆)alkylene;

[0136] R⁴⁸ is H, (C₁-C₈)alkyl, substituted or unsubstituted phenyl, orbenzyl which is unsubstituted or substituted on the phenyl ring;

[0137] R⁴⁹ is identical or different H, (C₁-C₈)alkyl, phenyl,phenyl(C₁-C₈)alkyl, it being possible for a phenyl ring to besubstituted by F, Cl, Br, NO₂, CN, OCH₃, (C₁-C₄)alkyl or CH₃SO₂—, or is(C₁-C₄)alkoxy-(C₁-C₈)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl,(C₃-C₆)cycloalkyl or two radicals R⁴⁹ together are (C₄-C₅)alkylene, itbeing possible for one CH₂ group to be replaced by O or S or for one ortwo CH₂ groups to be replaced by —NR^(d)—;

[0138] R^(d) is H or (C₁-C₄)alkyl;

[0139] m″ is 0 or 1 and

[0140] p is 0,1 or 2;

[0141] inclusive of the stereoisomers and of the salts conventionallyused in agriculture.

[0142] Herbicidally effective amount means, for the purposes of theinvention, an amount of one or more herbicides which is suitable foradversely affecting plant growth.

[0143] Antidote-effective amount means, for the purposes of theinvention, an amount of one or more safeners which is suitable for atleast partially counteracting the phytotoxic effect of a herbicide orherbicide mixture on a useful plant.

[0144] Unless specifically defined otherwise, the following definitionsgenerally apply to the radicals in formulae (I) to (VIII) and thesubsequent formulae.

[0145] The radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino andalkylthio and the corresponding unsaturated and/or substituted radicalsin the carbon skeleton can each be straight-chain or branched.

[0146] Alkyl radicals, also in the composite meanings such as alkoxy,haloalkyl and the like, preferably have 1 to 4 carbon atoms and are, forexample, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl. Alkenyland alkynyl radicals have the meaning of the unsaturated radicals whichare possible and which correspond to the alkyl radicals; alkenyl is, forexample, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and1-methylbut-2-en-1-yl. Alkynyl is, for example, propargyl,but-2-in-1-yl, but-3-in-1-yl, 1-methylbut-3-in-1-yl. “(C₁-C₄)-Alkyl” isthe abbreviation for alkyl having 1 to 4 carbon atoms; this also appliesanalogously to other general definitions of radicals whose ranges of thepossible number of carbon atoms is given in brackets.

[0147] Cycloalkyl is preferably a cyclic alkyl radical having 3 to 8,preferably 3 to 7, especially preferably 3 to 6, carbon atoms, forexample cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.Cycloalkenyl and cycloalkynyl denote corresponding unsaturatedcompounds.

[0148] Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl,-alkenyl and -alkynyl are alkyl, alkenyl or alkynyl which are partiallyor fully substituted by halogen, preferably fluorine, chlorine and/orbromine, in particular by fluorine or chlorine, for example CF₃, CHF₂,CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl. Haloalkoxy is, forexample, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ and OCH₂CH₂Cl. This alsoapplies analogously to other halogen-substituted radicals.

[0149] An aliphatic hydrocarbon radical is, generally, a straight-chainor branched saturated or unsaturated hydrocarbon radical, preferablyhaving 1 to 18, especially preferably 1 to 12, carbon atoms, for examplealkyl, alkenyl or alkynyl. Aryl is, generally, a mono-, bi- orpolycyclic aromatic system having preferably 6 to 14 carbon atoms,preferably phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl,pentalenyl and fluorenyl, especially preferably phenyl. An aliphatichydrocarbon radical preferably means alkyl, alkenyl or alkynyl having upto 12 carbon atoms; this also applies analogously to an aliphatichydrocarbon radical in a hydrocarbonoxy radical.

[0150] A heterocyclic ring, heterocyclic radical or heterocyclyl denotesa mono-, bi- or polycyclic ring system which is saturated, unsaturatedand/or aromatic and has one or more, preferably 1 to 4, hetero atoms,preferably selected from the group consisting of N, S and O.

[0151] Preferred are saturated heterocycles having 3 to 7 ring atoms andone or two hetero atoms selected from the group consisting of N, O andS, chalcogens not being adjacent. Especially preferred are monocyclicrings having 3 to 7 ring atoms and one hetero atom selected from thegroup consisting of N, O and S, and also morpholine, dioxolane,piperazine, imidazoline and oxazolidine. Very especially preferredsaturated heterocycles are oxirane, pyrrolidone, morpholine andtetrahydrofuran.

[0152] Also preferred are partially unsaturated heterocycles having 5 to7 ring atoms and one or two hetero atoms selected from the groupconsisting of N, O and S. Especially preferred are partially unsaturatedheterocycles having 5 to 6 ring atoms and one hetero atom selected fromthe group consisting of N, O and S.

[0153] Very especially preferred partially unsaturated heterocycles arepyrazoline, imidazoline and isoxazoline.

[0154] Also preferred are mono- or bicyclic aromatic heterocycles having5 to 6 ring atoms which contain one to four hetero atoms selected fromthe group consisting of N, O, S, chalcogens not being adjacent.Especially preferred are monocyclic aromatic heterocycles having 5 to 6ring atoms and containing a hetero atom selected from the groupconsisting of N, O and S, and also pyrimidine, pyrazine, pyridazine,oxazole, thiazole, thiadiazole, oxadiazole, pyrazole, triazole andisoxazole. Very especially preferred are pyrazole, thiazole, triazoleand furan.

[0155] Substituted radicals such as substituted hydrocarbon radicals,for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl andarylalkyl such as benzyl, or substituted heterocyclyl or heteroaryl, area substituted radical derived from the unsubstituted skeleton, thesubstituents preferably being one or more, preferably 1, 2 or 3, in thecase of Cl and F also up to the maximum possible number of, radicalsselected from the group consisting of halogen, alkoxy, haloalkoxy,alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido,alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- anddialkylaminocarbonyl, substituted amino such as acylamino, mono- anddialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl andhaloalkyl, and unsaturated aliphatic radicals corresponding to theabovementioned saturated hydrocarbon-containing radicals, preferablyalkenyl, alkynyl, alkenyloxy, alkynyloxy. In the case of radicals withcarbon atoms, those having 1 to 4 carbon atoms, in particular 1 or 2carbon atoms, are preferred. Preferred are, as a rule, substitutentsselected from the group consisting of halogen, for example fluorine orchlorine, (C₁-C₄)alkyl, preferably methyl or ethyl, (C₁-C₄)haloalkyl,preferably trifluoromethyl, (C₁-C₄)alkoxy, preferably methoxy or ethoxy,(C₁-C₄)haloalkoxy, nitro and cyano. Especially preferred are thesubstituents methyl, methoxy and chlorine.

[0156] Mono- or disubstituted amino denotes a chemically stable radicalselected from the group consisting of the substituted amino radicalswhich are N-substituted, for example, by one or two identical ordifferent radicals selected from the group consisting of alkyl, alkoxy,acyl and aryl, preferably monoalkylamino, dialkylamino, acylamino,arylamino, N-alkyl-N-arylamino and N-heterocycles. Alkyl radicals having1 to 4 carbon atoms are preferred. Aryl is preferably phenyl orsubstituted phenyl. As far as acyl is concerned, the definition givenfurther below applies, preferably (C₁-C₄)alkanoyl. This also appliesanalogously to substituted hydroxylamino or hydrazino.

[0157] Optionally substituted phenyl is, preferably, phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, in the case of halogen such as Cl and F also up topentasubstituted, by identical or different radicals selected from thegroup consisting of (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy and nitro, for example o-, m- and p-tolyl,dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and-trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- andp-methoxyphenyl.

[0158] An acyl radical denotes the radical of an organic acid preferablyhaving up to 6 carbon atoms, for example the radical of a carboxylicacid and radicals of acids derived therefrom such as of thiocarboxylicacid, optionally N-substituted iminocarboxylic acids, or the radical ofcarbonic monoesters, optionally N-substituted carbamic acids, sulfonicacids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, forexample, formyl, alkylcarbonyl such as (C₁-C₄-alkyl)carbonyl,phenylcarbonyl, it being possible for the phenyl ring to be substituted,for example as indicated above for phenyl, or alkyloxycarbonyl,phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl orN-alkyl-1-iminoalkyl.

[0159] The formulae (I) to (VIII) also encompass all stereoisomers whoseatoms have the same topological linkage, and mixtures of thesestereoisomers. Such compounds contain one or more asymmetric carbonatoms or else double bonds which are not especially mentioned in theformulae. The possible stereoisomers which are defined by their specificspatial form, such as enantiomers, diastereomers, Z- and E-isomers, maybe obtained by customary methods from stereoisomer mixtures or else beprepared by stereoselective reactions in combination with the use ofstereochemically pure starting materials.

[0160] Suitable herbicidal active substances according to the inventionare those compounds of the formula (I) which, by themselves, cannot beemployed, or not optimally employed, in cereal crops and/or maizebecause they are too harmful for the crop plants.

[0161] Herbicides,of the formula (I) are disclosed, for example, in

[0162] EP-A 0 496 631, WO-A 97/13 765,

[0163] WO-A 97/01 550, WO-A 97/19 087,

[0164] WO-A 96/30 368, WO-A 96/31 507,

[0165] WO-A 96/26 192, WO-A 96/26 206,

[0166] WO-A 96/10 561, WO-A 96/05 183,

[0167] WO-A 96/05 198, WO-A 96/05 197,

[0168] WO-A 96/05 182, WO-A 97/23 491 and

[0169] WO-A 97/27 187.

[0170] The cited publications contain extensive information onpreparation processes and starting materials. These publications arereferred to expressly and they are incorporated herein by reference.

[0171] The compounds of the formula (II) are disclosed, for example, inEP-A-0 333 131 (ZA-89/1960), EP-A-0 269 806 (U.S. Pat. No. 4,891,057),EP-A-0 346 620 (AU-A-89/34951), EP-A-0 174 562, EP-A-0 346 620(WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 94/7120) and inthe literature cited therein or can be prepared by or analogously to theprocesses described therein. The compounds of the formula (III) aredisclosed in EP-A-0 086 750, EP-A-0 94349 (U.S. Pat. No. 4,902,340),EP-A-0 191736 (U.S. Pat. No. 4,881,966) and EP-A-0 492 366 and in theliterature cited therein or can be prepared by or analogously to theprocesses described therein. Some compounds are furthermore described inEP-A-0 582 198. The compounds of the formula (II) are disclosed in alarge number of patent applications, for example U.S. Pat. No. 4,021,224and U.S. Pat. No. 4,021,229. Compounds of group (b) are furthermoreknown from CN-A-87/102 789, EP-A-365484 and from “The Pesticide Manual”,The British Crop Protection Council and the Royal Society of Chemistry,11th edition, Farnham 1997.

[0172] The compounds of group (c) are described in WO-A-97/45016, thoseof group (d) in German Patent Application 197 42 951.3, and those ofgroup (e) in WO-A 98/13 361.

[0173] The cited publications contain extensive information onpreparation processes and starting materials. These publications arereferred to expressly and they are incorporated herein by reference.

[0174] Preferred herbicide/safener combinations are those which comprisesafeners of the formula (II) and/or (III) in which the symbols andindices have the following meanings:

[0175] R²⁴ is hydrogen, (C₁-C₁₈)alkyl, (C₃-C₁₂)cycloalkyl,(C₂-C₈)alkenyl and (C₂-C₁₈)alkynyl, it being possible for thecarbon-containing groups to be substituted by one or more, preferably upto three, radicals R⁵⁰;

[0176] R⁵⁰ is identical or different halogen, hydroxyl, (C₁-C₈)alkoxy,(C₁-C₈)alkylthio, (C₂-C₈)alkenylthio, (C₂-C₈)alkynylthio,(C₂-C₈)alkenyloxy, (C₂-C₈)alkynyloxy, (C₃-C₇)cycloalkyl,(C₃-C₇)cycloalkoxy, cyano, mono- and di(C₁-C₄)alkyl)amino, carboxyl,(C₁-C₈)alkoxycarbonyl, (C₂-C₈)alkenyloxycarbonyl,(C₁-C₈)alkylthiocarbonyl, (C₂-C₈)alkynyloxycarbonyl,(C₁-C₈)alkylcarbonyl, (C₂-C₈)alkenylcarbonyl, (C₂-C₈)alkynylcarbonyl,1-(hydroxyimino)(C₁-C₆)alkyl, 1-[(C₁-C₄)alkylimino](C₁-C₄)alkyl,1-[(C₁-C₄)alkoxyimino](C₁-C₆)alkyl, (C₁-C₈)alkylcarbonylamino,(C₂-C₈)alkenylcarbonylamino, (C₂-C₈)alkynylcarbonylamino, aminocarbonyl,(C₁-C₈)alkylaminocarbonyl, di(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, (C₂-C₆)alkynylaminocarbonyl,(C₁-C₈)alkoxycarbonylamino, (C₁-C₈)alkylaminocarbonylamino,(C₁-C₆)alkylcarbonyloxy, which is unsubstituted or substituted by R⁵¹,(C₂-C₆)alkenylcarbonyloxy, (C₂-C₆)alkynylcarbonyloxy,(C₁-C₈)alkylsulfonyl, phenyl, phenyl(C₁-C₆)alkoxy,phenyl(C₁-C₆)alkoxycarbonyl, phenoxy, phenoxy(C₁-C₆)alkoxy,phenoxy(C₁-C₆)alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonylamino,phenyl(C₁-C₆)-alkylcarbonylamino, it being possible for thelast-mentioned 9 radicals to be unsubstituted or mono- orpolysubstituted in the phenyl ring, preferably up to trisubstituted, byradicals R^(52.); SiR′₃, —O—SiR′₃, R′₃Si—(C₁-C₈)alkoxy, —CO—O—NR′₂,—O—N═CR′₂, —N═CR′₂, —O—NR′₂, —NR′₂, CH(OR′)₂, —O—(CH₂)_(m)—CH(OR′)₂,—CR′″(OR′)₂, —O—(CH₂)_(m)CR′″(OR″)₂ or by R″O—CHR′″CHCOR″—(C₁-C₆)alkoxy,

[0177] R⁵¹ is identical or different halogen, nitro, (C₁-C₄)alkoxy andphenyl which is unsubstituted or substituted by one or more, preferablyup to three, radicals R⁵²;

[0178] R⁵² is identical or different halogen, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy or nitro;

[0179] R′ is identical or different hydrogen, (C₁-C₄)alkyl, phenyl whichis unsubstituted or substituted by one or more, preferably up to three,radicals R⁵², or two radicals R′ together form a (C₂-C₆)alkanediylchain;

[0180] R″ is identical or different (C₁-C₄)alkyl or two radicals R″together form a (C₂-C₆)alkanediyl chain;

[0181] R′″ is hydrogen or (C₁-C₄)alkyl;

[0182] m is 0, 1, 2, 3, 4, 5 or 6.

[0183] Especially preferred are herbicide/safener combinations accordingto the invention comprising safener of the formula (II) and/or (III)where the symbols and indices have the following meanings:

[0184] R²⁴ is hydrogen, (C₁-C₈)alkyl or (C₃-C₇)cycloalkyl, theabovementioned carbon-containing radicals being unsubstituted or mono-or polysubstituted by halogen or mono- or disubstituted, preferablymonosubstituted, by radicals R⁵⁰,

[0185] R⁵⁰ is identical or different hydroxyl, (C₁-C₄)alkoxy, carboxyl,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₂-C₆)alkynyloxycarbonyl, 1-(hydroxyimino)(C₁-C₄)alkyl,1-[(C₁-C₄)alkylimino](C₁-C₄)alkyl and 1-[(C₁-C₄)alkoxyimino](C_(1-C)₄)alkyl; —SiR′₃, —O—N═CR′₂, —N═CR′₂, —NR′₂, and —O—NR′₂, in which R′ isidentical or different hydrogen, (C₁-C₄)alkyl or, as a pair, a(C₄-C₅)alkanediyl chain,

[0186] R²⁷, R²⁸, R²⁹ are identical or different hydrogen, (C₁-C₈)alkyl,(C₁-C₆)haloalkyl, (C₃-C₇)cycloalkyl or phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, cyano, nitro, amino, mono- and di[(C₁-C₄)alkyl]amino,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio and (C₁-C₄)alkylsulfonyl;

[0187] R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy)(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₇)cycloalkyl ortri(C₁-C₄)alkylsilyl,

[0188] R¹⁷, R¹⁹ are identical or different hydrogen, halogen, methyl,ethyl, methoxy, ethoxy, (C₁ or C₂)haloalkyl, preferably hydrogen,halogen or (C₁ or C₂)haloalkyl.

[0189] Very especially preferred safeners are those in which the symbolsand indices in formula (II) have the following meanings:

[0190] R¹⁷ is hydrogen, halogen, nitro or (C₁-C₄)haloalkyl;

[0191] n′ is 1, 2 or 3;

[0192] R¹⁸ is a radical of the formula OR²⁴,

[0193] R²⁴ is hydrogen, (C₁-C₈)alkyl or (C₃-C₇)cycloalkyl, the abovecarbon-containing radicals being unsubstituted or mono- orpolysubstituted, preferably up to trisubstituted, by identical ordifferent halogen radicals or up to disubstituted, preferablymonosubstituted by identical or different radicals selected from thegroup consisting of hydroxyl, (C₁-C₄)alkoxy, (C₁-C₄)alkoxycarbonyl,(C₂-C₆)alkenyloxycarbonyl, (C₂-C₆)alkynyloxycarbonyl,1-(hydroxyimino)(C₁-C₄)alkyl, 1-[(C₁-C₄)alkylimino](C₁-C₄)alkyl,1-[(C₁-C₄)alkoxyimino](C₁-C₄)alkyl and radicals of the formulae —SiR′₃,—O—N═R′₂, —N═CR′₂, —NR′₂ and —O—NR′₂, the radicals R′ in theabovementioned formulae being identical or different hydrogen,(C₁-C₄)alkyl or, in pairs, (C₄ or C₅)alkanediyl;

[0194] R²⁷, R²⁸, R²⁹ are identical or different hydrogen, (C₁-C₈)alkyl,(C₁-C₆)haloalkyl, (C₃-C₇)cycloalkyl or phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, nitro, (C₁-C₄)haloalkyl and(C₁-C₄)haloalkoxy, and

[0195] R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₇)cycloalkyl ortri(C₁-C₄)alkylsilyl.

[0196] Very especially preferred safeners are also those of the formula(III) in which the symbols and indices have the following meanings:

[0197] R¹⁹ is hydrogen, halogen or (C₁-C₄)haloalkyl;

[0198] n′ is 1, 2 or 3, where (R¹⁹)_(n′) is preferably 5-Cl;

[0199] R²⁰ is a radical of the formula OR²⁴;

[0200] T is CH₂ and

[0201] R²⁴ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl or(C₁-C₄)alkoxy(C₁-C₄)alkyl, preferably (C₁-C₈)alkyl.

[0202] Particularly preferred are the safeners of the formula (II) inwhich the symbols and indices have the following meanings:

[0203] W is (W1);

[0204] R¹⁷ is hydrogen, halogen or (C₁-C₂)haloalkyl;

[0205] n′ is 1, 2 or 3, (R¹⁷)_(n′) preferably being 2,4-Cl₂;

[0206] R¹⁸ is a radical of the formula OR²⁴;

[0207] R²⁴ is hydrogen, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)hydroxyalkyl, (C₃-C₇)cycloalkyl, (C₁-C₄)alkoxy(C₁-C₄)alkyl ortri(C₁-C₂)alkylsilyl, preferably (C₁-C₄)alkyl;

[0208] R²⁷ is hydrogen, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl or(C₃-C₇)cycloalkyl, preferably hydrogen or (C₁-C₄)alkyl, and

[0209] R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)hydroxyalkyl, (C₃-C₇)cycloalkyl, (C₁-C₄)alkoxy(C₁-C₄)alkyl ortri(C₁-C₂)alkylsilyl, preferably hydrogen or (C₁-C₄)alkyl.

[0210] Also particularly preferred are herbicidal compositionscomprising a safener of the formula (II) where the symbols and indiceshave the following meanings:

[0211] W is (W2);

[0212] R¹⁷ is hydrogen, halogen or (C₁-C₂)haloalkyl;

[0213] n′ is 1, 2 or 3, (R¹⁷)_(n′) preferably being 2,4-Cl₂;

[0214] R¹⁸ is a radical of the formula OR²⁴;

[0215] R²⁴ is hydrogen, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)hydroxyalkyl, (C₃-C₇)cycloalkyl, (C₁-C₄)alkoxy)-C₁-C₄-alkyl ortri(C₁-C₂)alkylsilyl, preferably (C₁-C₄)alkyl, and

[0216] R²⁷ is hydrogen, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl,(C₃-C₇)cycloalkyl or phenyl, preferably hydrogen or (C₁-C₄)alkyl.

[0217] Also particularly preferred are safeners of the formula (II)where the symbols and indices have the following meanings:

[0218] W is (W3);

[0219] R¹⁷ is hydrogen, halogen or (C₁-C₂)haloalkyl;

[0220] n′ is 1, 2 or 3, (R¹⁷)_(′) preferably being 2,4-Cl₂;

[0221] R¹⁸ is a radical of the formula OR²⁴;

[0222] R²⁴ is hydrogen, (C₁-C₈)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)hydroxyalkyl, (C₃-C₇)cycloalkyl, (C₁-C₄)alkoxy(C₁-C₄)alkyl ortri(C₁-C₂)alkylsilyl, preferably (C₁-C₄)alkyl, and

[0223] R²⁸ is (C₁-C₈)alkyl or (C₁-C₄)haloalkyl, preferably C₁-haloalkyl.

[0224] Also particularly preferred are safeners of the formula (II)where the symbols and indices have the following meanings:

[0225] W is (W4);

[0226] R¹⁷ is hydrogen, halogen, nitro, (C₁-C₄)alkyl, (C₁-C₂)haloalkyl,preferably CF₃ or (C₁-C₄)alkoxy;

[0227] n′ is 1, 2 or 3;

[0228] m′ is 0 or 1;

[0229] R¹⁸ is a radical of the formula OR²⁴;

[0230] R²⁴ is hydrogen, (C₁-C₄)alkyl, carboxy(C₁-C₄)alkyl,(C₁-C₄)alkoxycarbonyl-(C₁-C₄)alkyl, preferably (C₁-C₄)alkoxy-CO—CH₂—,(C₁-C₄)alkoxy-CO—C(CH₃)H—, HO—CO—CH₂— or HO—CO—C(CH₃)H—, and

[0231] R²⁹ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₃-C₇)cycloalkyl or phenyl which is unsubstituted or substituted by oneor more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, nitro, cyano and (C₁-C₄)alkoxy.

[0232] The following groups of compounds are particularly suitable assafeners for the herbicidal active substances of the formula (I):

[0233] a) compounds of the dichlorophenylpyrazoline-3-carboxylic acidtype (i.e. of the formula (II), where W═W1 and (R¹⁷)_(n′)=2,4-Cl₂),preferably compounds such as ethyl1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate(II-1), and related compounds as they are described in WO-A 91/07874;

[0234] b) dichlorophenylpyrazolecarboxylic acid derivatives (i.e. of theformula (II), where W═(W2) and (R¹⁷)_(n′)=2,4-Cl₂), preferably compoundssuch as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate(II-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate(II-3), ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate(II-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate(II-5) and related compounds as they are described in EP-A-0 333 131 andEP-A-0 269 806.

[0235] c) Compounds of the triazolecarboxylic acid type (i.e. of theformula (II), where W═(W3) and (R¹⁷)_(n′)=2,4-Cl₂), preferably compoundssuch as fenchlorazol, i.e. ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate(II-6), and related compounds (see EP-A-0 174 562 and EP-A-0 346 620);

[0236] d) compounds of the 5-benzyl- or5-phenyl-2-isoxazoline-3-carboxylic acid type or the5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (where W═(W4)),preferably compounds such as ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (II-7) or ethyl5-phenyl-2-isoxazoline-3-carboxylate (II-8) and related compounds asthey are described in WO-A-91/08202, or of the ethyl5,5-diphenyl-2-isoxazolinecarboxylate type (II-9), the n-propyl5,5-diphenyl-2-isoxazolinecarboxylate type (II-10) or the ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate type (II-11), asthey are described in WO-A-95/07897.

[0237] e) Compounds of the 8-quinolinoxyacetic acid type, for examplethose of the formula (III), where (R¹⁹)_(n′)=5-Cl, hydrogen, R²⁰═OR²⁴and T═CH₂, preferably the compounds

[0238] 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (III-1,cloquintocet),

[0239] 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (III-2),

[0240] 4-allyloxy-butyl (5-chloro-8-quinolinoxy)acetate (III-3),

[0241] 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (III-4),

[0242] ethyl (5-chloro-8-quinolinoxy)acetate (III-5),

[0243] methyl (5-chloro-8-quinolinoxy)acetate (III-6),

[0244] allyl (5-chloro-8-quinolinoxy)acetate (III-7),

[0245] 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate(III-8),

[0246] 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (III-9)

[0247] and related compounds as they are described in EP-A-0 860 750,EP-A-0 094 349 and EP-A-0 191 736 or EP-A-0 492 366.

[0248] f) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type,i.e. of the formula (III), where (R¹⁷)_(n′)=5-Cl, R²⁰═OR²⁴,T═—CH(COO-alkyl)-, preferably the compounds diethyl(5-chloro-8-quinolinoxy)malonate, diallyl(5-chloro-8-quinolinoxy)malonate, methyl ethyl(5-chloro-8-quinolinoxy)malonate and related compounds as they aredescribed in EP-A-0 582 198.

[0249] g) compounds of the dichloroacetamide type, i.e. of the formula(IV), preferably:

[0250] N,N-diallyl-2,2-dichloroacetamide (dichlormid, disclosed in U.S.Pat. No. 4,137,070),

[0251] 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine(benoxacor, disclosed in EP 0 149 974),

[0252] N¹,N²-diallyl-N²-dichloroacetylglycinamide (DKA-24, disclosed inHU 2143821),

[0253] 4-dichloroacetyl-1-oxa-4-aza-spiro[4,5]decane (AD-67),

[0254] 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292),

[0255] 3-dichloroacetyl-2,2,5-trimethyloxazolidine,

[0256] 3-dichloroacetyl-2,2-dimethyl-5-phenyloxazolidine,

[0257] 3-dichloroacetyl-2,2-dimethyl-5-(2-thienyl)oxazolidine,

[0258] 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine(furilazole, MON 13900),

[0259]1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidine-6(2H)-one(dicyclonon, BAS 145138),

[0260] h) compounds of group B(b), preferably

[0261] 1,8-naphthalic anhydride,

[0262] methyl diphenylmethoxyacetate,

[0263] cyanomethoxyimino(phenyl)acetonitrile (cyometrinil),

[0264] 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil),

[0265] 4′-chloro-2,2,2-trifluoroacetophenoneO-1,3-dioxolan-2-ylmethyloxime (fluxofenim),

[0266] 4,6-dichloro-2-phenylpyrimidine (fenclorim),

[0267] benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate(flurazole),

[0268] 2-dichloromethyl-2-methyl-1,3-dioxolan (MG-191),

[0269] N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron),

[0270] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0271] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0272] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,

[0273] 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0274] (2,4-dichlorophenoxy)acetic acid (2,4-D),

[0275] (4-chlorophenoxy)acetic acid,

[0276] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

[0277] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

[0278] (4-chloro-o-tolyloxy)acetic acid (MCPA),

[0279] 4-(4-chloro-o-tolyloxy)butyric acid,

[0280] 4-(4chlorophenoxy)butyric acid,

[0281] 3,6-dichloro-2-methoxybenzoic acid (dicamba),

[0282] 1-(ethoxycarbonyl)ethyl 3,6dichloro-2-methoxybenzoate(lactidichlor)

[0283] and their salts and esters, preferably (C₁-C₈).

[0284] Furthermore preferred as safeners are compounds of the formula(V) or their salts, where

[0285] R³⁰ is hydrogen, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl, furanyl orthienyl, it being possible for each of the last-mentioned 4 radicals tobe unsubstituted or substituted by one or more substituents selectedfrom the group consisting of halogen, (C₁-C₄)alkoxy, halo(C₁-C₆)alkoxyand (C₁-C₄)alkylthio and, in the case of cyclic radicals, also(C₁-C₄)alkyl and (C₁-C₄)haloalkyl,

[0286] R³¹ is hydrogen,

[0287] R³² is halogen, halo(C₁-C₄)alkyl, halo(C₁-C₄)alkoxy,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylsulfonyl, (C₁-C₄)alkoxycarbonylor (C₁-C₄)alkylcarbonyl, preferably halogen, (C₁-C₄)haloalkyl, such astrifluoromethyl, (C₁-C₄)alkoxy, halo(C₁-C₄)alkoxy, (C₁-C₄)alkoxycarbonylor (C₁-C₄)alkylsulfonyl,

[0288] R³³ is hydrogen,

[0289] R³⁴ is halogen, (C₁-C₄)alkyl, halo(C₁-C₄)alkyl,halo(C₁-C₄)alkoxy, (C₃-C₆)cycloalkyl, phenyl, (C₁-C₄)alkoxy, cyano,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkoxycarbonyl or (C₁-C₄)alkylcarbonyl, preferably halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, such as trifluoromethyl,halo(C₁-C₄)alkoxy, (C₁-C₄)alkoxy or (C₁-C₄)alkylthio,

[0290] n is 0, 1 or 2 and

[0291] m is 1 or 2.

[0292] Furthermore preferred are safeners of the formula (VI), in which

[0293] X³ is CH;

[0294] R³⁵ is hydrogen, (C₁-C₆)alkyl, (C₃-C₆)cycloalkyl, (C₂-C₆)alkenyl,(C₅-C₆)cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl having upto three hetero atoms selected from the group consisting of nitrogen,oxygen and sulfur, it being possible for the six last-mentioned radicalsto be optionally substituted by one or more identical or differentsubstituents selected from the group consisting of halogen,(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₂)alkylsulfinyl,(C₁-C₂)alkylsulfonyl, (C₃-C₆)cycloalkyl, (C₁-C₄)alkoxycarbonyl,(C₁-C₄)alkylcarbonyl and phenyl and, in the case of cyclic radicals,also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl;

[0295] R³⁶ is hydrogen, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, itbeing possible for the three last-mentioned radicals optionally to besubstituted by one or more, identical or different substituents selectedfrom the group consisting of halogen, hydroxyl, (C₁-C₄)alkyl,(C₁-C₄)alkoxy and (C₁-C₄)alkylthio;

[0296] R³⁷ is halogen, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, nitro,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylsulfonyl, (C₁-C₄)alkoxycarbonylor (C₁-C₄)alkylcarbonyl;

[0297] R³⁸ is hydrogen;

[0298] R³⁹ is halogen, nitro, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy, (C₃-C₆)cycloalkyl, phenyl, (C₁-C₄)alkoxy, cyano,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkoxycarbonyl or (C₁-C₄)alkylcarbonyl;

[0299] n is 0, 1 or 2 and

[0300] m is 1 or 2.

[0301] Especially preferred amongst the safeners of the formula (VII)are the sub-groups which follow:

[0302] compounds in which R⁴⁸ and R⁴⁹ are H, (C₁-C₈)alkyl, phenyl,phenyl(C₁-C₈)alkyl, (C₁-C₄)alkoxy-(C₁-C₈)alkyl, (C₃-C₆)alkenyl or(C₃-C₆)alkynyl, it being possible for phenyl rings to be substituted byF, Cl, Br, NO₂, CN, OCH₃, (C₁-C₄)alkyl or CH₃—SO₂—;

[0303] compounds in which R^(a) is H;

[0304] compounds in which A is R^(b)—Y³;

[0305] compounds in which E is O;

[0306] compounds in which Q¹ is CR₂ ⁴⁷;

[0307] compounds in which R⁴⁷ is H;

[0308] compounds in which m″ is 1 and E is O or S;

[0309] compounds in which m″=0;

[0310] compounds in which R⁴⁰ to R⁴⁴ are H, m″ is 1, E is O, Q¹ is CR₂⁴⁷ and A is R^(b)—Y³, in particular those where R⁴⁷ is H, R^(b) is CH₃and Y³ is O;

[0311] compounds in which Q¹ is CR₂ ⁴⁷ and m equals 0, in particularthose in which R⁴⁴ and R⁴⁷ are H and A is R^(b)—Y³ where R^(b) ispreferably methyl and Y³ is preferably O.

[0312] Preferred groups of herbicides of the formula (I) are listed inTables 1 to 16 which follow. TABLE 1 (V = V1, Z = Z1):

Ex. R R1 (R9)₉ R10 1-1 H c-Pr 4-SEt 2-Bzl 1-2 H c-Pr 4-SMe 2-Bzl 1-3 Hc-Pr 4-F-3-Me 2-(4-Cl-Bzl) 1-4 H c-Pr 4-SMe 2-(2-Me-Bzl) 1-5 H c-Pr4-SO₂Me 2-(2-Cl-Bzl) 1-6 H c-Pr 4-SO₂Me 2-(3-Cl-Bzl) 1-7 H c-Pr 4-SO₂Me2-(4-Cl-Bzl) 1-8 H c-Pr 4-SO₂Me 2-(1-triazolyl) 1-9 COOEt c-Pr 4-SO₂Me2-(1-triazolyl) 1-10 COOMe c-Pr 4-SO₂Me 2-(1-triazolyl) 1-11 H c-Pr4-SO₂Me 2-(1-pyrazolyl) 1-12 COOEt c-Pr 4-SO₂Me 2-(1-pyrazolyl) 1-13COOMe c-Pr 4-SO₂Me 2-(1-pyrazolyl) 1-14 H c-Pr 4-SO₂Me2-(3,5-DiMe-1-pyrazolyl) 1-15 COOEt c-Pr 4-SO₂Me2-(3,5-DiMe-1-pyrazolyl) 1-16 COOMe c-Pr 4-SO₂Me2-(3,5-DiMe-1-pyrazolyl) 1-17 H 1-Me-c-Pr 4-SO₂Me 2-(1-triazolyl) 1-18COOEt 1-Me-c-Pr 4-SO₂Me 2-(1-pyrazolyl) 1-19 COOMe 1-Me-c-Pr 4-SO₂Me2-(3,5-DiMe-1-pyrazolyl) 1-20 H c-Pr 2-Cl-4-SO₂Me 3-(1-triazolyl) 1-21COOEt c-Pr 4-CF₃ 2-(CH2-1-triazolyl) 1-22 H c-Pr 4-CF₃ 2-[CH2—PO(OEt)2]1-23 H c-Pr 4-CF₃ 2-[CH2—PO(OMe)2] 1-24 H c-Pr 3-Br 2-[CH2—PO(OMe)2]1-25 COOEt c-Pr 4-Br 2-[CH2—PO(OEt)2] 1-26 COOEt c-Pr 3,4-DiCl2-[CH2—PO(OMe)2] 1-27 COOEt c-Pr 4-Br 2-[CH2—PO(OMe)2] 1-28 COOEt c-Pr4-CF₃ 2-[CH2—PO(OMe)2] 1-29 H C-Pr 2-Cl-4-SO₂Me 3-(2-thiazolyl) 1-30COOEt C-Pr 2-Cl-4-SO₂Me 3-(2-thiazolyl) 1-31 H 1-Me-c-Pr 2-Cl-4-SO₂Me3-(2-thiazolyl) 1-32 COOEt 1-Me-c-Pr 2-Cl-4-SO₂Me 3-(2-thiazolyl) 1-33 Hc-Pr — 4-SF₅

[0313] TABLE 2 (V = V2, Z = Z1):

Ex. R2 R3 R4 (R9)₉ R10 2-1 H H Me 2-Cl-4-SO₂Me 3-(2-thiazolyl) 2-2 Me HMe 2-Cl-4-SO₂Me 3-(2-thiazolyl) 2-3 H SO₂Me Me 2-Cl-4-SO₂Me3-(2-thiazolyl) 2-4 H SO₂-(4-Me—Ph) Me 2-Cl-4-SO₂Me 3-(2-thiazolyl)

[0314] TABLE 3 (V = V3, Z = Z1):

Ex. (R5)_(o) R6 (R9)₉ R10 3-1 — OH 2-Cl-4-SO₂Me 3-(2-thiazolyl) 3-25-(CH(OMe)₂) OH 2-Cl-4-SO₂Me 3-(2-thiazotyl) 3-3 — OH 4-Cl-2-SO₂Me3-(2-thiazolyl) 3-4 5-(CH(OMe)₂) OH 4-Cl-2-SO₂Me 3-(2-thiazolyl) 3-55,5-DiMe OH 2-Me-4-SO₂Me 3-(2-furanyl) 3-6 5,5-DiMe OH 2-Cl-4-SO₂Me3-(2-furanyl) 3-7 — OH 2-Me-4-SO₂Me 3-(2-furanyl) 3-8 — OH 2-Cl-4-SO₂Me3-(2-furanyl) 3-9 — OH 2-Cl-4-SO₂Me 3-CH2OMe 3-10 — OH 2-Cl-4-SO₂Me3-[CH2—CH(OMe)2] 3-11 — OH 2-Cl-4-SO₂Me 3-O-C2H4-OMe 3-12 — OH 2,4-DiCl3-O—CH2-(1,3- dioxolan-4-yl) 3-13 — OH 2-Cl-4-SO₂Me3-(2-isoxazolin-3-yl) 3-14 — OH 2-Cl-4-SO₂Me 3-(1-pyrazolylmethyl) 3-15— OH 2-Cl-4-SO₂Me 3-morpholinyl

[0315] TABLE 4 (V = V4, Z = Z1):

Ex. R7 R8 (R9)₉ R10 4-1 c-Pr CN 4-S—Et 2-Bzl 4-2 c-Pr CN 4-S—Me 2-Bzl4-3 c-Pr CN 4-F-3-Me 2-(4-Cl-Bzl) 4-4 c-Pr CN 4-S—Me 2-(2-Me-Bzl) 4-5c-Pr CN 4-SO₂Me 2-(2-Cl-Bzl) 4-6 c-Pr CN 4-SO₂Me 2-(3-Cl-Bzl) 4-7 c-PrCN 4-SO₂Me 2-(4-Cl-Bzl) 4-8 c-Pr CN 4-Br 2-(1-pyrazolyl) 4-9 c-Pr CN3,4-DiCl 2-(CH2-1-triazolyl) 4-10 c-Pr CN 4-Br 2-[CH2PO(OEt)2] 4-11 c-PrCN 4-Br 2-[CH2PO(OMe)2] 4-12 c-Pr CN — 2-[CH2PO(OEt)2] 4-13 c-Pr CN —2-[CH2PO(OMe)2] 4-14 c-Pr CN 2-Cl-4-SO₂Me 3-(2-thiazolyl) 4-15 1-Me-c-PrCN 2-Cl-4-SO₂Me 3-(2-thiazolyl) 4-16 t-Bu CN 2-Cl-4-SO₂Me3-(2-thiazolyl)

[0316] TABLE 5 (V = V1, Z = Z2)

Ex. R R1 X¹ X² [C(R11)2]_(t) (R12)_(r) 5-1 H c-Pr C(OC₂H₄O) SO₂ C₂H₄2,5-DiMe 5-2 H c-Pr CHOMe SO₂ C₂H₄ 2-Me-5-Cl 5-3 H c-Pr O O CF₂2-[CH₂PO(OMe)₂] 5-4 COOEt c-Pr O O CF₂ 2-[CHCH₃PO(OEt)₂] 5-5 COOEt1-Me-c-Pr O O CF₂ 2-[CH₂PO(OMe)₂] 5-6 COOEt c-Pr O O CF₂2-[CHCH₃PO(OMe)₂] 5-7 H c-Pr C(SC₂H₄S) SO₂ C₂H₄ 2,5-DiMe 5-8 H c-PrC(SC₂H₄S) SO₂ C₂H₄ 2-Me-5-Cl 5-9 H c-Pr C(CH₃)₂ SO₂ C₂H₄ 2,5-DiMe 5-10 Hc-Pr CHOMe SO₂ C₂H₄ 2,5-DiMe 5-11 H c-Pr CHOC₂H₄F SO₂ C₂H₄ 2,5-DiMe 5-12H c-Pr C═NOMe SO₂ C₂H₄ 2,5-DiMe 5-13 H c-Pr C═NOMe SO₂ C₂H₄ 2-Me 5-14 Hc-Pr C═NOMe S C₂H₄ 2,5-DiMe

[0317] TABLE 6 (V = V2, Z = Z2):

[C (R11) Ex. R2 R3 R4 X¹ X² 2]_(t) (R12)_(r) 6-1 H H Et C(OC₂H₄O) SO₂C₂H₄ 2,5-DiMe 6-2 H H Et CHOMe SO₂ C₂H₄ 2-Me-5-Cl 6-3 H H Me C(OC₂H₄O)SO₂ C₂H₄ 2,5-DiMe 6-4 H H Me CHOMe SO₂ C₂H₄ 2-Me-5-Cl 6-5 H H Et CO SO₂C₂H₄ 2,5-DiMe 6-6 H H Et CO SO₂ C₂H₄ 2-Me-5-Cl 6-7 H SO₂Me Et C(OC₂H₄O)SO₂ C₂H₄ 2,5-DiMe 6-8 H SO₂Me Et CHOMe SO₂ C₂H₄ 2-Me-5-Cl 6-9 H SO₂Me MeC(OC₂H₄O) SO₂ C₂H₄ 2,5-DiMe 6-10 H SO₂Me Me CHOMe SO₂ C₂H₄ 2-Me-5-Cl6-11 H SO₂Me Et CO SO₂ C₂H₄ 2,5-DiMe 6-12 H SO₂Me Et CO SO₂ C₂H₄2-Me-5-Cl 6-13 Me SO₂-(4-Me— Me C═NOMe SO₂ C₂H₄ 2,5-DiMe —Ph) 6-14 MeCH₂—CO—Ph Me C═NOMe SO₂ C₂H₄ 2,5-DiMe

[0318] TABLE 7 (V = V3, Z = Z2)

Ex. R5 R6 X¹ X² [C(R11)2]_(t) (R12)_(r) 7-1 — OH C(OC₂H₄O) SO₂ C₂H₄2,5-DiMe 7-2 — OH CHOMe SO₂ C₂H₄ 2-Me-5-Cl 7-3 4,4-DiMe OH C(OC₂H₄O) SO₂C₂H₄ 2,5-DiMe 7-4 4,4-DiMe OH CHOMe SO₂ C₂H₄ 2-Me-5-Cl 7-5 — OHC(OC₂H₄O) SO₂ C₂H₄ — 7-6 — OH CHOMe SO₂ C₂H₄ — 7-7 — OH CO SO₂ C₂H₄2,5-DiMe 7-8 — OH CO SO₂ C₂H₄ 2-Me-5-Cl 7-9 — OH C(OC₂H₄O) SO₂ C₂H₄2,5-DiCl 7-10 — OH C(SC₂H₄S) SO₂ C₂H₄ 2,5-DiMe 7-11 5-(CH OH C(OC₂H₄O)SO₂ C₂H₄ 2,5-DiMe (OMe)2) 7-12 5-(CH OH CHOMe SO₂ C₂H₄ 2,5-DiMe (OMe)2)7-13 — OH C═NOH SO₂ C₂H₄ — 7-14 — OH CHOMe SO₂ C₂H₄ 2,5-DiMe

[0319] TABLE 8 (V = V4, Z = Z2):

Ex. R7 R8 X¹ X² [C(R11)2]_(t) (R12)_(r) 8-1 c-Pr CN C(OC₂H₄O) SO₂ C₂H₄2,5-DiMe 8-2 c-Pr CN CHOMe SO₂ C₂H₄ 2-Me-5-Cl 8-3 1-Me-c-Pr CN C(OC₂H₄O)SO₂ C₂H₄ 2,5-DiMe 8-4 1-Me-c-Pr CN CHOMe SO₂ C₂H₄ 2-Me-5-Cl 8-5 c-Pr CNC(SC₂H₄S) SO₂ C₂H₄ 2,5-DiMe 8-6 c-Pr CN C(SC₂H₄S) SO₂ C₂H₄ 2-Me-5-Cl 8-7c-Pr CN C(CH₃)₂ SO₂ C₂H₄ 2,5-DiMe 8-8 c-Pr CN CHOMe SO₂ C₂H₄ 2,5-DiMe8-9 c-Pr CN CHOC₂H₄F SO₂ C₂H₄ 2,5-DiMe 8-10 c-Pr CN C═NOMe SO₂ C₂H₄2,5-DiMe 8-11 c-Pr CN C═NOMe SO₂ C₂H₄ 2-Me 8-12 c-Pr CN C═NOMe S C₂H₄2,5-DiMe

[0320] TABLE 9 (V = V1, Z = Z3):

Ex. R R1 Y1 Y2 (R12)_(r) R13 9-1 H c-Pr SO₂ CO — Me 9-2 H c-Pr SO₂ CO —H 9-3 COOEt c-Pr SO₂ CO — Me 9-4 COOEt c-Pr SO₂ CO — H 9-5 H 1-Me-c-PrSO₂ CO — Me 9-6 H 1-Me-c-Pr SO₂ CO — H 9-7 COOEt 1-Me-c-Pr SO₂ CO — Me9-8 COOEt 1-Me-c-Pr SO₂ CO — H 9-9 H 1-SMe-c-Pr SO₂ CO — Me 9-10 H1-SMe-c-Pr SO₂ CO — H 9-11 COOEt 1-SMe-c-Pr SO₂ CO — Me 9-12 COOEt1-SMe-c-Pr SO₂ CO — H 9-13 H c-Pr CO SO₂ — Me 9-14 COOEt c-Pr CO SO₂ —Me 9-15 H 1-Me-c-Pr CO SO₂ — Me 9-16 COOEt 1-Me-c-Pr CO SO₂ — Me 9-17 H1-SMe-c-Pr CO SO₂ — Me 9-18 COOEt 1-SMe-c-Pr CO SO₂ — Me

[0321] TABLE 10 (V = V2, Z = Z3):

Ex. R2 R3 R4 Y1 Y2 (R12)_(r) R13 10-1 H H Et SO₂ CO — Me 10-2 H H Et SO₂CO — H 10-3 Me H Et SO₂ CO — Me 10-4 Me H Et SO₂ CO — H 10-5 H H Me SO₂CO — Me 10-6 H H Me SO₂ CO — H 10-7 Me H Me SO₂ CO — Me 10-8 Me H Me SO₂CO — H 10-9 H H Me CO SO₂ — Me 10-10 H H Me CO SO₂ — H 10-11 Me H Me COSO₂ — Me 10-12 Me H Me CO SO₂ — H 10-13 Me H Me CO SO₂ 2-Me Me

[0322] TABLE 11 (V = V3, Z = Z3):

Ex. (R5)o R6 Y1 Y2 (R12)_(r) R13 11-1 — OH SO₂ CO — Me 11-2 — OH SO₂ CO— H 11-3 4,4-DiMe OH SO₂ CO — Me 11-4 4,4-DiMe OH SO₂ CO — H 11-5 — OHCO SO₂ — Me 11-6 — OH CO SO₂ — H 11-7 4,4-DiMe OH CO SO₂ — Me 11-84,4-DiMe OH CO SO₂ — H

[0323] TABLE 12 (V = V4, Z = Z3):

Ex. R7 R8 Y1 Y2 (R12)_(r) R13 12-1 c-Pr CN SO₂ CO — Me 12-2 c-Pr CN SO₂CO — H 12-3 1-Me-c-Pr CN SO₂ CO — Me 12-4 1-Me-c-Pr CN SO₂ CO — H 12-5c-Pr CN CO SO₂ — Me 12-6 c-Pr CN CO SO₂ — H 12-7 1-Me-c-Pr CN CO SO₂ —Me 12-8 1-Me-c-Pr CN CO SO₂ — H

[0324] TABLE 13 (V = V1, Z = Z4):

Ex. R R1 v U² (R¹²)_(r) U¹ (R¹⁶)_(n) 13-1 H c-Pr 1 SO₂ 2,5- DiMe

— 13-2 H c-Pr 1 SO₂ 2,5- DiMe

— 13-3 H c-Pr 2 SO₂ 2,5- DiMe

— 13-4 H c-Pr 2 SO₂ 2,5- DiMe

— 13-5 H 1-Me-c-Pr 1 SO₂ 2,5- DiMe

— 13-6 H 1-Me-c-Pr 1 SO₂ 2,5- DiMe

—

[0325] TABLE 14 (V = V2, Z = Z4):

Ex. R2 R3 R4 v U² (R¹²)_(r) U¹ (R¹⁶)_(n) 14-1 H H Et 1 SO₂ 2,5-DiMe

— 14-2 H H Et 1 SO₂ 2,5-DiMe

— 14-3 H SO₂-(4-Me)Ph Et 1 SO₂ 2,5-DiMe

— 14-4 H SO₂Me Et 1 SO₂ 2,5-DiMe

— 14-5 H H Et 1 SO₂ 2,5-DiMe

— 14-6 H H Et 2 SO₂ 2,5-DiMe

— 14-7 H H Et 2 SO₂ 2,5-DiMe

— 14-8 H H Me 1 SO₂ 2,5-DiMe

— 14-9 H H Me 1 SO₂ 2,5-DiMe

—

[0326] TABLE 15 (V = V3, Z = Z4):

Ex. (R5)_(o) R6 V U² (R¹²)_(r) U¹ (R¹⁶)_(n) 15-1 — OH 1 SO₂ 2,5- DiMe

— 15-2 — OH 1 SO₂ 2,5- DiMe

— 15-3 — OH 1 SO₂ 2,5- DiMe

— 15-4 5-Me OH 1 SO₂ 2,5- DiMe

— 15-5 5-Me OH 2 SO₂ 2,5- DiMe

— 15-6 — OH 1 SO₂ 2,5- DiMe

— 15-7 — OH 2 SO₂ 2,5- DiMe

—

[0327] TABLE 16 (V = V4, Z = Z4);

Ex. R7 R8 V U² (R¹²)_(r) U¹ (R¹⁶)_(n) 16-1 c-Pr CN 1 SO2 2,5- DiMe

— 16-2 1-Me-c-Pr CN 1 SO2 2,5- DiMe

— 16-3 c-Pr CN 1 SO2 2,5- DiMe

— 16-4 1-Me-c-Pr CN 1 SO2 2,5- DiMe

—

[0328] The safeners (antidotes) of the formulae (II)-(VII) and thecompounds of group for example safeners of the abovementioned groups a)to h), reduce or prevent phytotoxic effects which may occur when usingthe herbicidal active substances of the formula (I) in crops of usefulplants without substantially affecting the efficacy of these herbicidalactive substances against harmful plants. This allows the field ofapplication of conventional crop protection products to be widened quiteconsiderably and to be extended to, for example, crops such as wheat,barley, maize and other crops in which use of the herbicides washitherto impossible, or only limited, that is to say at low rates andwith a restricted spectrum.

[0329] The herbicidal active substances and the mentioned safeners canbe applied together (as a readymix or by the tank mix method) or insuccession in any desired sequence. The weight ratio ofsafener:herbicidal active substance may vary within wide limits and ispreferably in the range of from 1:100 to 100:1, in particular 1:10 to10:1. The optimum amounts of herbicidal active substance and safenerwhich are used in each case depend on the type of the herbicidal activesubstance used or on the safener used and on the species of the cropstand to be treated and can be determined in each individual case bysimple routine preliminary experiments.

[0330] The main fields of application for the combinations according tothe invention are, in particular, maize and cereal crops such as, forexample, wheat, rye, barley, oats, rice, sorghum, but also cotton andsoybeans, preferably cereals, rice and maize.

[0331] Depending on their properties, the safeners employed inaccordance with the invention can be used for pretreating the seed of acrop plant (seed dressing), or be incorporated into the seed furrowsprior to sowing or applied together with the herbicide before or afterplant emergence. The pre-emergence treatment includes not only treatmentof the area under cultivation prior to sowing and treatment of the areasunder cultivation where the seeds have been planted but the plants havenot yet emerged. The joint application together with the herbicide ispreferred. To this end, tank mixes or readymixes may be employed.

[0332] The application rates of safener required may vary within widelimits depending on indication and herbicidal active substance used andare generally in the range of from 0.001 to 5 kg, preferably 0.005 to0.5 kg, of active substance per hectare.

[0333] The present invention therefore also relates to a method ofprotecting crop plants from phytotoxic side effects of herbicides of theformula (I) which comprises applying an antidote-effective amount of acompound of the formula (II), (III), (IV), (V), (VI), (VII) and/or(selected from the group (b)) to the plants, plant seeds or the areaunder cultivation, either before, after or simultaneously with, theherbicidal active substance A of the formula (I).

[0334] The herbicide/safener combination according to the invention mayalso be employed for controlling harmful plants in crops of geneticallyengineered plants which are either known or still to be developed. As arule, the transgenic plants are distinguished by particular,advantageous properties, for example by resistance to certain cropprotection agents, resistance to plant diseases or pathogens causingplant diseases such as particular insects or microorganisms such asfungi, bacteria or viruses. Other particular properties relate, forexample, to the harvested material in terms of quantity, quality,storing properties, composition and specific constituents. Thus, thereare known transgenic plants with an increased starch content or with analtered starch quality, or those where the harvested material has adifferent fatty acid composition.

[0335] The use of the combinations according to the invention ineconomically important transgenic crops of useful plants andornamentals, for example cereals such as wheat, barley, rye, oats,sorghum and millet, rice, cassava and maize, or else crops of sugarbeet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and othervegetables.

[0336] When the combinations according to the invention are applied intransgenic crops, effects on harmful plants to be observed in othercrops are frequently accompanied by effects which are specific forapplication in the transgenic crop in question, for example an alteredor specifically widened weed spectrum which can be controlled, alteredapplication rates which may be used, preferably good compatibility withthe herbicides to which the transgenic crop is resistant, and alteredgrowth and yield of the transgenic crop plants.

[0337] The invention therefore also relates to the use of thecombination according to the invention for controlling harmful plants intransgenic crop plants.

[0338] The safeners of the formulae (III)-(VII) and of group (b) andtheir combinations with one or more of the abovementioned herbicidalactive substances of the formula (II) can be formulated in various ways,depending on the biological and/or chemico-physical parametersspecified. Examples of possible formulations which are suitable are:

[0339] Wettable powders (WP), emulsifiable concentrates (EC),water-soluble powders (SP), water-soluble concentrates (SL),concentrated emulsions (BW) such as oil-in-water and water-in-oilemulsions, sprayable solutions or emulsions, capsule suspensions (CS),oil- or water-based dispersions (SC), suspoemulsions, suspensionconcentrates, dusts (DP), oil-miscible solutions (OL), seed-treatmentproducts, granules (GR) in the form of microgranules, spray granules,coated granules and adsorption granules, granules for soil applicationor broadcasting, water-soluble granules (SG), water-dispersible granules(WG), ULV formulations, microcapsules and waxes.

[0340] These individual formulation types are known in principle anddescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4^(th) Edition1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker N.Y.,1973; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. GoodwinLtd. London.

[0341] The formulation auxiliaries which may be required, such as inertmaterials, surfactants, solvents and other additives are also known anddescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H.v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-Active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], Volume 7, C. HauserVerlag Munich, 4^(th) Edition 1986.

[0342] Based on these formulations, it is also possible to preparecombinations with other substances which act as crop protection agents,such as insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a readymix or tank mix.

[0343] Wettable powders are preparations which are uniformly dispersiblein water and which, besides the active substance, also comprise ionicand/or nonionic surfactants (wetting agents, dispersants), for examplepolyoxyethylated alkylphenols, polyoxyethylated fatty alcohols,polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates,alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate, or else sodium oleoylmethyltaurinate, inaddition to a diluent or inert substance. To prepare the wettablepowders, the herbicidally active substances are ground finely, forexample in customary apparatus such as hammer mills, blower mills andair-jet mills, and simultaneously or subsequently mixed with theformulation auxiliaries.

[0344] Emulsifiable concentrates are prepared, for example, bydissolving the active substance in an organic solvent, such as butanol,cyclohexanone, dimethylformamide, or else higher-boiling hydrocarbonssuch as saturated or unsaturated aliphatic hydrocarbons or alicyclichydrocarbons, aromatics or mixtures of the organic solvents with theaddition of one or more ionic and/or nonionic surfactants (emulsifiers).Examples of substances which can be used as emulsifiers are: calciumalkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionicemulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycolethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxidecondensates, alkyl polyethers, sorbitan esters, for example sorbitanfatty acid esters or polyoxyethylene sorbitan esters, for examplepolyoxyethylene sorbitan fatty acid esters.

[0345] Dusts are generally obtained by grinding the active substancewith finely distributed solid substances, for example talc, naturalclays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0346] Suspension concentrates can be water- or oil-based. They can beprepared, for example, by wet grinding using commercially available beadmills with or without an addition of surfactants, for example thosewhich have already been mentioned above in the case of the otherformulation types.

[0347] Emulsions, for example oil-in-water emulsions (EW), can beprepared, for example, by means of stirrers, colloid mills and/or staticmixers using aqueous organic solvents in the presence or absence ofsurfactants which have already been mentioned above, for example, in thecase of the other formulation types.

[0348] Granules can be prepared either by spraying the active substanceonto adsorptive, granulated inert material or by applying activesubstance concentrates to the surface of carriers such as sand,kaolinites or granulated inert material with the aid of binders, forexample polyvinyl alcohol, sodium polyacrylate or else mineral oils.Suitable active substances can also be granulated in the manner which isconventional for the preparation of fertilizer granules, if desired as amixture with fertilizers. As a rule, water-dispersible granules areprepared by the customary processes such as spray drying, fluidized bedgranulation, disk granulation, mixing with high-speed mixers, andextrusion without solid inert material.

[0349] For the preparation of disk, fluidized-bed, extruder and spraygranules see, for example, processes in “Spray-Drying Handbook” 3^(rd)Ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”,Chemical and Engineering 1967, pages 147 et seq.; “Perry's ChemicalEngineer's Handbook”, b 5 ^(th) Ed., McGraw-Hill, New York 1973, p.8-57.

[0350] For further details on the formulation of crop protectionproducts see, for example, G. C. Klingman, “Weed Control as a Science”,John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer,S. A. Evans, “Weed Control Handbook”, 5^(th) Ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

[0351] As a rule, the agrochemical preparations comprise 0.1 to 99% byweight, in particular 0.1 to 95% by weight, of active substances of theformula (II)-(VII) and/or (b) or of the herbicide/antidote mixture ofactive substances (I) and (II)-(VII) and/or (b) and 1 to 99.9% byweight, in particular 5 to 99.8% by weight of a solid or liquid additiveand 0 to 25% by weight, in particular 0.1 to 25% by weight of asurfactant.

[0352] In wettable powders, the active substance concentration is, forexample, approximately 10 to 90% by weight, the remainder to 100% byweight being composed of customary formulation components. In the caseof emulsifiable concentrates, the concentration of active substance isapproximately 1 to 80% by weight. Formulations in the form of dustscomprise 1 to 20% by weight of active substance, sprayable solutionscomprise approximately 0.2 to 20% by weight of active substance. In thecase of granules, such as water-dispersible granules, the activesubstance content depends partly on whether the active compound is inliquid or solid form. The active substance content of thewater-dispersible granules is, for example, between 10 and 90% byweight.

[0353] Besides this the abovementioned formulations of active substancesmay comprise, if appropriate, the adhesives, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agents,solvents, fillers, carriers, colorants, antifoams, evaporationinhibitors and pH and viscosity regulators which are customary in eachcase.

[0354] Components which can be used in combination with theherbicide/safener mixtures according to the invention in mixedformulations or in tank mixes are, for example, known active substancesas they are described, for example, in Weed Research 26, 441-445 (1986),or “The Pesticide Manual”, 10^(th) edition, The British Crop ProtectionCouncil, 1994, and the literature cited therein. Examples of activesubstances which may be mentioned as herbicides which are known from theliterature and which can be combined with the mixtures according to theinvention are the following (note: either the common names in accordancewith the International Organization for Standardization (ISO) or thechemical names, if appropriate together with a customary code number, ofthe compounds are given): acetochlor; acifluorfen; aclonifen; AKH 7088,i.e.[[[1-[5-[2-chloro4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]aceticacid and its methyl ester; alachlor; alloxydim; ametryn; amidosulfuron;amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazine;azafenidine (DPX-R6447), azimsulfuron (DPX-A8947); aziprotryn; barban;BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin;benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone;benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox;bispyribac-sodium (KIH-2023), bromacil; bromobutide; bromofenoxim;bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos;butenachlor; buthidazole; butralin; butroxydim (ICI-0500), butylate;cafenstrole (CH-900); carbetamide; cafentrazone; CDAA, i.e.2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyldiethyldithiocarbamate; chlomethoxyfen; chloramben; chloransulam-methyl(XDE-565), chlorazifop-butyl, chlorbromuron; chlorbufam; chlorfenac;chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen;chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron;chlorthal-dimethyl; chlorthiamid; cinidonethyl, cinmethylin;cinosulfuron; clefoxydim, clethodim; clodinafop and its esterderivatives (e.g. clodinafop-propargyl); clomazone; clomeprop;cloproxydim; clopyralid; cumyluron (JC 940); cyanazine; cycloate;cyclosulfamuron (AC 014); cycloxydim; cycluron; cyhalofop and its esterderivatives (e.g. butyl ester, DEH-112); cyperquat; cyprazine;cyprazole; 2,4-DB; dalapon; desmedipham; desmetryn; diallate; dicamba;dichlobenil; dichlorprop; diclofop and its esters such asdiclofopmethyl; diclosulam (XDE-564), diethatyl; difenoxuron;difenzoquat; diflufenican; diflufenzopyr-sodium (SAN-835H), dimefuron;dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone,5-(4,6-dimethylpyrimidin-2-yl-carbamoylsulfamoyl)-1-(2-pyridyl)-pyrazole4-carboxylate(NC-330); clomazon; dimethipin; dimetrasulfuron, dinitramine; dinoseb;dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC;eglinazine-ethyl; EL 177, i.e.5cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide;endothal; epoprodan (MK-243), EPTC; esprocarb; ethalfluralin;ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; F5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide;ethoxyfen and its esters (e.g. ethyl ester, HN-252); ethoxysulfuron(disclosed in EP 342569) etobenzanid (HW 52);3-(4-ethoxy-6-ethyl-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]thiophene-7-sulfonyl)urea(EP-A 079 683);3-(4ethyl-6-methoxy-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]thiophene-7-sulfonyl)urea(EP-A 079 683); fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and theiresters, e.g. fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim;fentrazamide (NBA-061); fenuron; flamprop-methyl; flazasulfuron;flufenacet (BAY-FOE-5043), fluazifop and fluazifop-P, florasulam(DE-570) and their esters, e.g. fluazifop-butyl and fluazifop-P-butyl;fluazolate (Mon-48500), fluchloralin; flucarbazone-sodium; flumetsulam;flumeturon; flumiclorac and their esters (e.g. pentyl ester, S-23031);flumioxazin (S-482); flumipropyn; flupoxam (KNW-739); fluorodifen;fluoroglycofen-ethyl; flupropacil (UBIC-4243); flupyrsulfuron-methylsodium (DPX-KE459), fluridone; flurochloridone; fluroxypyr; flurtamone;fluthiacet-methyl (KIH-9201), fomesafen; fosamine; furyloxyfen;glufosinate; glyphosate; halosafen; halosulfuron and its esters (e.g.methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P(=R-haloxyfop) and its esters; hexazinone; imazamethabenz-methyl;imazamox (AC-299263), imazapyr; imazaquin and salts such as the ammoniumsalt; imazethamethapyr; imazethapyr; imazosulfuron; iodosulfuron(methyl-4-iodo-2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl]-benzoate,sodium salt, WO 92/13845); ioxynil; isocarbamid; isopropalin;isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate; lactofen;lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid;metamitron; metazachlor; methabenzthiazuron; metham; methazole;methoxyphenone; methyldymron; metobenzuron,methyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methanesulfonamidomethylbenzoate(WO 95/10507); methobenzuron; metobromuron; metolachlor; S-metolachlor,metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH;molinate; monalide; monocarbamide dihydrogensulfate; monolinuron;monuron; MT 128, i.e.6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide;N,N-dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-formylaminobenzamide(WO 95/01344); naproanilide; napropamide; naptalam; NC 310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon;nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrofluorfen;norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon;oxaziclomefone (MY-100), oxyfluorfen; oxasulfuron (CGA-277476),paraquat; pebulate; pendimethalin; pentoxazone (KPP-314), perfluidone;phenisopham; phenmedipham; picloram; piperophos; piributicarb;pirifenop-butyl; pretilachlor; primisulfuron-methyl;pracarbazone-sodium; procyazine; prodiamine; profluralin;proglinazine-ethyl; prometon; prometryn; propachlor; propanil;propaquizafop and its esters; propazine; propham; propisochlor;propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005);prynachlor; pyraflufen-ethyl (ET-751), pyrazon; pyrazosulfuron-ethyl;pyrazoxyfen; pyribenzoxim, pyridafol; pyridate; pyriminobac-methyl(KIH6127), pyrithiobac (KIH-2031); pyroxofop and its esters (e.g.propargyl ester); quinclorac; quinmerac; quinofop and its esterderivatives, quizalofop and quizalofop-P and their ester derivativese.g. quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron;rimsulfuron (DPX-E 9636); S 275, i.e.2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e.2-[[7-[2-chloro4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]-propanoicacid and its methyl ester; sulfentrazon (FMC-97285, F6285); sulfazuron;sulfometuron-methyl; sulfosate (ICI-A0224); sulfosulfuron (MON-37500),TCA; tebutam (GCP-5544); tebuthiuron; tepraloxydim (BAS-620H), terbacil;terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450,i.e.N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide;thenylchlor (NSK-850); thiazafluron; thiazopyr (Mon-13200); thidiazimin(SN-124085); thifensulfuron-methyl; thiobencarb; thiocarbazil;tralkoxydim; tri-allate; triasulfuron, triaziflam (DH-1105);triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine;trifluralin; triflusulfuron and esters (e.g. methyl ester, DPX-66037);trimeturon; tsitodef; vernolate; WL 110547, i.e.5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; UBH-509; D489; LS82-556; KPP-300; KPP-421, MT-146, NC-324; KH-218; DPX-N8189; DOWCO-535;DK-8910; V-53482; PP-600; MBH-001.

[0355] For use, the formulations which are in commercially availableform are, if desired, diluted in the customary manner, for example usingwater in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules. Preparations in the form ofdusts, soil granules, granules for broadcasting and sprayable solutionsare usually not diluted any further with other inert substances prior touse.

[0356] The necessary application rate of the herbicides of the formula(I) varies with the external conditions such as, inter alia,temperature, humidity and the nature of the herbicide used. It may bevaried within wide limits, for example between 0.001 and 10.0 kg/ha ormore of active ingredient, but it is preferably between 0.005 and 5kg/ha.

[0357] The examples which follow are intended to illustrate theinvention:

A. FORMULATION EXAMPLES

[0358] a) A dust is obtained by mixing 10 parts by weight of a compoundof the formula (II)-(VII) and/or (from amongst group (b)) or of anactive substance mixture of a herbicidal active substance of the formula(I) and a safener of the formula (II)-(VII) and/or from amongst group(b) and 90 parts by weight of talc as inert substance and comminutingthe mixture in a hammer mill.

[0359] b) A wettable powder which is readily dispersible in water isobtained by mixing 25 parts by weight of a compound of the formula (II),(III), (IV) and/or (B(b)) or of an active substance mixture of aherbicidal active substance of the formula (I) and a safener of theformula (II), (III), (IV) and/or from amongst group B(b), 64 parts byweight of kaolin-containing quartz as inert material, 10 parts by weightof potassium lignosulfonate and 1 part by weight of sodiumoleoylmethyltaurinate as wetter and dispersant and grinding the mixturein a pinned-disk mill.

[0360] c) A dispersion concentrate which is readily dispersible in wateris obtained by mixing 20 parts by weight of a compound of the formula(II)-(VII) and/or from amongst group (b) or of an active substancemixture of a herbicidal active substance of the formula (I) and asafener of the formula (II)-(VII) and/or from amongst group (b), 6 partsby weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts byweight of isotridecanol polyglycol ether (8 EO) and 71 parts by weightof paraffinic mineral oil (boiling range, for example, approx. 255 toabove 277° C.) and grinding the mixture in a ball mil to a fineness ofbelow 5 microns.

[0361] d) An emulsifiable concentrate is obtained from 15 parts byweight of a compound of the formula (II)-(VII) and/or from amongst group(b) or of an active substance mixture of a herbicidal active substanceof the formula (I) and a safener of the formula (II)-(VII) and/or fromamongst group (b), 75 parts by weight of cyclohexanone as solvent and 10parts by weight of ethoxylated nonylphenol as emulsifier.

[0362] e) Water-dispersible granules are obtained by mixing

[0363] 75 parts by weight of a compound of the formula (II)-(VII) and/orfrom amongst the group (b) or of an active substance mixture of aherbicidal active substance of the formula (I) and a safener of theformula (II)-(VII) and/or from amongst group b,

[0364] 10″ of calcium lignosulfonate

[0365] 5″ of sodium lauryl sulfate,

[0366] 3″ of polyvinyl alcohol and

[0367] 7″ of kaolin,

[0368] grinding the mixture on a pinned-disk mill and granulating thepowder in a fluidized bed by spraying on water as the granulationliquid.

[0369] f) Water-dispersible granules are also obtained by homogenizingand precomminuting, on a colloid mill,

[0370] 25 part(s) by weight of a compound of the formula (II)-(VII)and/or from amongst group (b) or of an active substance mixture of aherbicidal active substance of the formula (I) and a safener of theformula (II)-(VII) and/or from amongst group (b)

[0371] 5″ of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate

[0372] 2″ of sodium oleoylmethyltaurinate,

[0373] 1″ of polyvinyl alcohol,

[0374] 17″ of calcium carbonate and

[0375] 50″ of water,

[0376] subsequently grinding the mixture on a bead mill and atomizingand drying the resulting suspension in a spray tower by means of asingle-substance nozzle.

BIOLOGICAL EXAMPLES

[0377] 1. Scoring the Damage

[0378] The damage to the plants is assessed visually in comparison withcontrol plants using a scale of 0-100%:

[0379] 0%=no noticeable effect in comparison with the untreated plant,

[0380] 100%=treated plant dies.

[0381] 2. Pre-emergence Herbicide Action and Safener Action

[0382] Seeds of monocotyledonous and dicotyledonous weed plants of cropplants are placed in sandy loam soil in plastic pots of 9 cm diameterand covered with soil. Alternatively, weeds found in rice cultivationunder paddy rice conditions are, for the test, cultivated in waterloggedsoil, the pots being filled with such an amount of water that the waterreaches the soil surface or floods it by a few millimeters. The activesubstance combinations according to the invention, of herbicide andsafener, which are formulated as emulsion concentrates and, in parallelexperiments, the individual active substances formulated analogously arethen applied to the surface of the soil cover in the form of emulsionsat a water application rate of 300 l/ha (converted) or, in the case ofrice, poured into the irrigation water, in each case in various dosages.

[0383] After the treatment, the pots are placed in the greenhouse andkept under good growth conditions. After the test plants have emergedafter a test period of 34 weeks, the damage to the plants, or emergencedamage, is scored visually by comparison with untreated controls. Asillustrated by the test results, the herbicidal compositions accordingto the invention have a good herbicidal pre-emergence action against abroad spectrum of grass weeds and dicotyledonous weeds, while damage tocrop plants such as maize, rice, wheat or barley or other cereals ismarkedly reduced by comparison with the use of the individual herbicideswithout safener, i.e. the herbicide damage is reduced by 30% up to 100%.

[0384] 3. Post-emergence Herbicide Action and Safener Action

[0385] Seeds of monocotyledonous and dicotyledonous weed plants and ofcrop plants are placed in sandy loam soil in plastic pots, covered withsoil and grown in the greenhouse under good growth conditions.Alternatively, weeds found in rice cultivation and rice are grown, forthe test under paddy rice conditions, in pots in which water floods thesoil surface by up to 2 cm, and cultivated during the growth phase.Approx. three weeks after sowing, the test plants are treated in thethree-leaf stage. The active substance combinations according to theinvention of herbicide and safener which are formulated as emulsionconcentrates and, in parallel experiments, the individual activesubstances which are formed analogously are sprayed onto the green partsof the plants in various dosages at a water application rate of 300 l/ha(converted) and, after the test plants have been left in the greenhousefor three weeks under ideal growth conditions, the effect of theproducts was scored visually by comparison with untreated controls. Inthe case of rice or weeds found in rice cultivation, the activesubstances are also added direct to the irrigation water (applicationanalogously to the so-called granule application) or sprayed onto plantsand into the irrigation water. As the results, in particular those shownin Tables 17 and 18, demonstrate, the herbicidal compositions accordingto the invention have a goods herbicidal post-emergence activity againsta broad spectrum of grass weeds and dicotyledonous weeds, while damageto crop plants such as maize, rice, wheat or barley or other cereals ismarkedly reduced by comparison with the use of the individual herbicideswithout safener, i.e. the herbicide damage is reduced by 30% up to100%.. TABLE 17 Damage [%] in Compound No. Dosage [g/ha] wheat VarietyHerbicide/Safener Herbicide Safener “RALLE” 7-14 50 30 25 25

50 + 50 25 + 25  5  0

[0386] TABLE 18 Dosage [g/ha] Damage [%] in maize Compound No. HerbicideVariety Variety Herbicide/Safener Safener “FELIX” “DEA” 5-10 200 88 25 100 65 10   50 30 0

200 + 100 50 + 25 40  0 0 0

200 + 100 100 + 50  20  0 0 0

200 + 100 50 + 25 30  0 0 0

200 + 100 50 + 25 5 0 0 0

1. A herbicidally active composition comprising a mixture of A. aherbicidally active amount of one or more compounds of the formula (I)

 in which V is a radical selected from the group consisting of (V1) to(V4),

 where the symbols and indices have the following meanings: R ishydrogen, (C₁-C₄)alkoxycarbonyl, (C₁-C₄)haloalkoxycarbonyl, COOH, cyano;R′ is hydrogen or a (C₁-C₇)carbon-containing radical such as(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C7)cycloalkyl,(C₃-C₇)cycloalkenyl, (C₁-C₄)alkyl-(C₃-C₇)cycloalkyl,(C₃-C₇)halocycloalkyl, (C₁-C₄)alkylthiocycloalkyl, (C₁-C₄)haloalkyl,(C₂-C₄)haloalkenyl; R² is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkyl, halogen, (C₁-C₄)haloalkoxy, cyano, nitro; R³ ishydrogen or a (C₁-C₄)carbon-containing radical such as (C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, arylsulfonyl, arylcarbonyl-(C₁-C₄)alkyl,aryl(C₁-C₄)alkyl; R⁴ is hydrogen or a (C₁-C₇)carbon-containing radicalsuch as (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,phenyl, benzyl; R⁵ is a (C₁-C₁₂)carbon-containing radical such as(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₁-C₄)dialkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio, halogen, substituted orunsubstituted aryl, tetrahydropyran-4-yl, tetrahydropyran-3-yl,tetrahydrothiopyran-3-yl, 1-methylthio-cyclopropyl, 2-ethylthiopropyl;R⁶ is hydroxyl or a (C₁-C₄)carbon-containing radical such as(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, formyloxy, (C₁-C₄)alkylcarbonyloxy,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl; R⁷ is a(C₁-C₇)carbon-containing radical such as (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₃-C₇)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₇)cycloalkyl,(C₃-C₇)halocycloalkyl; R⁸ is cyano or a (C₁-C₄)carbon-containing radicalsuch as (C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylcarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylthio,(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)dialkylaminocarbonyl; m is an integerfrom 0 to 6; and Z is a radical selected from the group consisting of(Z1) to (Z4),

 where the symbols and indices have the following meanings: R⁹ is nitro,amino, halogen or a (C₁-C₈)carbon-containing radical such as(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,(C₂-C₄)haloalkenyl, (C₂-C₄)haloalkynyl, (C₁-C₄)haloalkoxy,(C₁-C₄)haloalkylthio, (C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylthio, arylsulfonyl, arylsulfinyl,arylthio, (C₁-C₄)alkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylaminosulfonyl,(C₁-C₄)dialkylaminosulfonyl, (C₁-C₄)alkylcarbamoyl,(C₁-C₄)dialkylcarbamoyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, phenoxy, cyano,aryl, alkylamino, dialkylamino; R¹⁰ is substituted or unsubstitutedbenzyl, substituted or unsubstituted heteroaryl, heterocyclyl,heteroaryl(C₁-C₄)alkyl, di(C₁-C₄)alkylphosphono(C₁-C₄)alkyl or SF₅; R¹¹is identical or different hydrogen, (C₁-C₄)alkyl, halogen; R¹² isidentical or different (C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,halogen, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl, (C₂-C₄)haloalkynyl,(C₁-C₄)haloalkoxy, (C₁-C₄)haloalkylthio, (C₁-C₄)alkoxycarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfinyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylthio, (C₁-C₄)alkoxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylaminosulfonyl,(C₁-C₄)dialkylaminosulfonyl, (C₁-C₄)alkylcarbamoyl,(C₁-C₄)dialkylcarbamoyl, (C₁-C₄)alkoxyalkyl, phenoxy, nitro, cyano,aryl, di-(C₁-C₄)alkylphosphono-(C₁-C₄)alkyl; q is 0, 1, 2, 3 or 4; r is0, 1, 2 or 3; t is 1 or 2; u is 0, 1 or 2; v is 1 or 2; X¹ is O,CR¹⁴R¹⁵, CHOH, C═O, C═NO(C₁-C₄)alkyl; X² is O, S, SO, SO₂, CH₂, NH,N(C₁-C₄)alkyl, NSO₂(C₁-C₄)alkyl; U¹ together with the linked carbonatoms forms a carbocyclic or heterocyclic ring which can be aromatic orfully or partially saturated; U² is O, S, SO, SO₂, CH₂, NH,N(C₁-C₄)alkyl, NSO₂(C₁-C₄)alkyl; R¹³ is hydrogen, (C₁-C₄)alkyl,(C₃-C₇)cycloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, optionallysubstituted phenyl, optionally substituted benzyl, (C₁-C₄)acyl; R¹⁴R¹⁵is identical or different hydrogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio or R¹⁴ and R¹⁵together form one of the groups —O—(CH₂)₂—O—, —O—(CH₂)₃—O—, S—(CH₂)₂—S—,—S—(CH₂)₃—S—, —(CH₂)₄—, —(CH₂)₅—; R¹⁶ is (C₁-C₂)alkyl Y¹, Y² are SO₂ orCO, with the proviso that Y¹≠Y², and B. an antidote-effective amount ofone or more compounds selected from the groups consisting of a) to e):a) compounds of the formulae (II) to (IV),

 where the symbols and indices have the following meanings: n′ is anatural number from 1 to 5, preferably 1 to 3 T is a (C₁ orC₂)-alkanediyl chain which is unsubstituted or substituted by one or two(C₁-C₄)alkyl radicals or by [(C₁-C₃)-alkoxy]carbonyl, W is anunsubstituted or substituted divalent heterocyclic radical selected fromthe group consisting of the partially unsaturated or aromaticfive-ringed heterocycles having 1 to 3 hetero ring atoms of the type Nor O, the ring containing at least one nitrogen atom and not more thanone oxygen atom; m′ is 0 or 1; R¹⁷, R¹⁹ are identical or differenthydrogen, halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, nitro or(C₁-C₄)haloalkyl; R¹⁸, R²⁰ are identical or different OR²⁴, SR²⁴ orNR²⁴R²⁵ or a saturated or unsaturated 3- to 7-membered heterocyclehaving at least one nitrogen atom and up to 3 hetero atoms which islinked to the carbonyl group in (II) or (III) via the nitrogen atom andwhich is unsubstituted or substituted by radicals from the groupconsisting of (C₁-C₄)alkyl, (C₁-C₄)alkoxy or optionally substitutedphenyl; R²⁴ is hydrogen or an unsubstituted or substituted aliphatichydrocarbon radical; R²⁵ is hydrogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy orsubstituted or unsubstituted phenyl; R²⁶ is hydrogen, (C₁-C₈)alkyl,(C₁-C₈)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl,(C₃-C₁₂)cycloalkyl or tri-(C₁-C₄)-alkylsilyl; R²⁷, R²⁸, R²⁹ areidentical or different hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₃-C₁₂)cycloalkyl or substituted or unsubstituted phenyl; R²¹ is(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₃-C₇)cycloalkyl; R²², R²³ is identical or different hydrogen,(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,(C₂-C₄)haloalkenyl, (C₁-C₄)alkylcarbamoyl-(C₁-C₄)alkyl,(C₂-C₄)alkenylcarbamoyl-(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,dioxolanyl-(C₁-C₄)alkyl, thiazolyl, furyl, furylalkyl, thienyl,piperidyl, substituted or unsubstituted phenyl, or R²² and R²³ togetherform a substituted or unsubstituted heterocyclic ring; b) one or morecompounds from the group consisting of: c) 1,8-naphthalic anhydride,methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile(cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile(oxabetrinil), 4′-chloro-2,2,2-trifluoroacetophenoneO-1,3-dioxolan-2-ylmethyloxime (fluxofenim),4,6-dichloro-2-phenylpyrimidine (fenclorim),benzyl-2-chloro4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole),2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron),1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea,(2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid,(R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),(4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyricacid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoicacid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6dichloro-2-methoxybenzoate(lactidichlor) and their salts and esters, c) N-acylsulfonamides of theformula (V) and their salts,

 where R³⁰ is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical,a hydrocarbonthio radical or a heterocyclyl radical, each of thelast-mentioned 4 radicals being unsubstituted or substituted by one ormore identical or different radicals selected from the group consistingof halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl,carboxamide, sulfonamide and radicals of the formula —Z^(a)—R^(a), R³¹is hydrogen or (C₁-C₄)alkyl, or R³⁰ and R³¹ together with the group ofthe formula —CO—N— are the radical of a 3- to 8-membered saturated orunsaturated ring; and R³² in the event that n=1, or the R³²independently of one another, in the event that n is greater 1, is ineach case halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl,CONH₂, SO₂NH₂ or a radical of the formula —Z^(b)—R^(b), R³³ is hydrogenor (C₁-C₄)alkyl; R³⁴ in the event that m=1, or the R³⁴ independently ofone another, in the event that m is greater than 1, is in each casehalogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH₂, SO₂NH₂ ora radical of the formula —Z^(c)—R^(c), R^(a) is a hydrocarbon radical ora heterocyclyl radical, each of the two last-mentioned radicals beingunsubstituted or substituted by one or more identical or differentradicals selected from the group consisting of halogen, cyano, nitro,amino, hydroxyl, mono- and di-[(C₁-C₄)alkyl]amino, or is an alkylradical in which more than one nonadjacent CH₂ groups are each replacedby an oxygen atom, R^(b), R^(c) independently of one another are ahydrocarbon radical or a heterocyclyl radical, each of the twolast-mentioned radicals being unsubstituted or substituted by one ormore identical or different radicals selected from the group consistingof halogen, cyano, nitro, amino, hydroxyl, phosphoryl,halo(C₁-C₄)alkoxy, mono- and di[(C₁-C₄)alkyl]amino, or are an alkylradical in which more than one nonadjacent CH₂ groups are each replacedby an oxygen atom, Z^(a) is a divalent group of the formula —O—, —S—,—Co—, —CS—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—,—CO—NR*—, —NR*—CO—, —SO₂—NR*— or —NR*—SO₂—, the bond shown on the rightof the divalent group in question being the bond to the radical R^(a)and the R* in the last-mentioned 5 radicals independently of one anotherbeing in each case H, (C₁-C₄)alkyl or halo(C₁-C₄)alkyl, Z^(b), Z^(c)independently of one another are a direct bond or a divalent group ofthe formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—,—SO₂—, —NR*—, —SO₂—NR*—, —NR*—SO₂—, —CO—NR*— or —NR*—CO—, the bond shownon the right of the divalent group in question being the bond to theradical R^(b) or R^(c), respectively, and the R* in the last-mentioned 5radicals independently of one another being in each case H, (C₁-C₄)alkylor halo(C₁-C₄)alkyl, n is an integer from 0 to 4, and m is an integerfrom 0 to
 5. d) Acylsulfamoylbenzamides of the formula (VI), ifappropriate in salt form,

 where X³ is CH or N; R³⁵ is hydrogen, heterocyclyl or a hydrocarbonradical, the two last-mentioned radicals optionally being substituted byone or more, identical or different radicals selected from the groupconsisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO,CONH₂, SO₂NH₂ and Z^(a)—R^(a); R³⁶ is hydrogen, hydroxyl, (C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy, thefive last-mentioned radicals optionally being substituted by one or moreidentical or different radicals selected from the group consisting ofhalogen, hydroxyl, (C₁-C₄)alkyl, (C₁-C₄)alkoxy and (C₁-C₄)alkylthio, orR³⁵ and R³⁶ together with the nitrogen atom to which they are attachedare a 3- to 8-membered saturated or unsaturated ring; R³⁷ is halogen,cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH₂, SO₂NH₂ orZ^(b)—R^(b); R³⁸ is hydrogen, (C₁-C₄)alkyl, (C₂-C₄)alkenyl or(C₂-C₄)alkynyl; R³⁹ is halogen, cyano, nitro, amino, hydroxyl, carboxyl,phosphoryl, CHO, CONH₂, SO₂NH₂ or Z^(c)—R^(c); R^(a) is a (C₂-C₂₀)alkylradical whose carbon chain is interrupted once or more by oxygen atoms,or is heterocyclyl or a hydrocarbon radical, the two last-mentionedradicals optionally being substituted by one or more, identical ordifferent radicals selected from the group consisting of halogen, cyano,nitro, amino, hydroxyl, mono- and di[(C₁-C₄)alkyl]amino; R^(b), R^(c)identical or different are a (C₂-C₂₀)alkyl radical whose carbon chain isinterrupted once or more by oxygen atoms, or are heterocyclyl or ahydrocarbon radical, the two last-mentioned radicals optionally beingsubstituted by one or more identical or different radicals selected fromthe group consisting of halogen, cyano, nitro, amino, hydroxyl,phosphoryl, (C₁-C₄)haloalkoxy, mono- and di[(C₁-C₄)-alkyl]amino; Z^(a)is a divalent unit selected from the group consisting of O, S, CO, CS,C(O)O, C(O)S, SO, SO₂, NR^(d), C(O)NR^(d) or SO₂NR^(d); Z^(b), Z^(c)independently of one another are a direct bond or a divalent unitselected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO,SO₂, NR^(d), SO₂NR^(d) or C(O)NR^(d); R^(d) is hydrogen, (C₁-C₄)alkyl or(C₁-C₄)haloalkyl; n is an integer from 0 to 4, and m, in the event thatX is CH, is an integer from 0 to 5 and, in the event that X is N, aninteger from 0 to 4; e) compounds of the formula (VII),

 where the symbols and indices have the following meanings: R⁴⁰ is H,(C₁-C₄)alkyl, (C₁-C₄)alkyl substituted by (C₁-C₄)alkyl-X⁴ or(C₁-C₄)haloalkyl-X⁴, (C₁-C₄)haloalkyl, NO₂, CN, —COO—R⁴³, NR₂ ⁴⁴, SO₂NR₂⁴⁵ or CONR₂ ⁴⁶; R⁴¹ is H, halogen, (C₁-C₄)alkyl, CF₃, (C₁-C₄)alkoxy or(C₁-C₄)haloalkoxy; R⁴² is H, halogen or (C₁-C₄)alkyl; Q¹, Q², E, G areidentical or different, —O—, —S—, —CR₂ ⁴⁷—, —CO—, NR⁴⁸— or a group ofthe formula (VII), C═CH—O—CR₂ ^(a)—(CO)—A  (VIII), with the proviso thata) at least one of the groups Q¹, Q², E, G is a carbonyl group, thatexactly one of this group is a radical of the formula (VIII) and thatthe group of the formula (VIII) is adjacent to a carbonyl group, and b)two adjacent groups Q¹, Q², E and G cannot simultaneously be oxygen;R^(a) is identical or different H or (C₁-C₈)alkyl or the two radicalsR^(a) together are (C₂-C₆)alkylene; A is R^(b)—Y— or —NR₂ ⁴⁹; X⁴ is —O—or —S(O)_(p)—; Y³ is —O— or —S—; R^(b) is H, (C₁-C₈)alkyl,(C₁-C₈)haloalkyl, (C₁-C₄)alkoxy(C₁-C₈)alkyl,(C₃-C₆)alkenyloxy(C₁-C₈)alkyl, or phenyl(C₁-C₈)alkyl, the phenyl ringoptionally being substituted by halogen, (C₁-C₄)alkyl, CF₃, methoxy ormethyl-S(O)_(p); (C₃-C₆)alkenyl, (C₃-C₆)haloalkenyl,phenyl(C₃-C₆)alkenyl, (C₃-C₆)alkynyl, phenyl(C₃-C₆)alkynyl, oxetanyl,furfuryl, tetrahydrofuryl; R⁴³ is H or (C₁-C₄)alkyl; R⁴⁴ is identical ordifferent H, (C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl or the two radicals R⁴⁴together are (C₄-C₅)alkylene; R⁴⁵, R⁴⁶ are identical or different H,(C₁-C₄)alkyl, or the two radicals R⁴⁵ and/or R⁴⁶ together are(C₄-C₅)alkylene, it being possible for one CH₂ group to be replaced by Oor S or for one or two CH₂ groups to be replaced by —NR²—; R^(c) is H or(C₁-C₈)alkyl; R⁴⁷ is identical or different H, (C₁-C₈)alkyl or the tworadicals R⁴⁷ together are (C₂-C₆)alkylene; R⁴⁸ is H, (C₁-C₈)alkyl,substituted or unsubstituted phenyl, or benzyl which is unsubstituted orsubstituted on the phenyl ring; R⁴⁹ is identical or different H,(C₁-C₈)alkyl, phenyl, phenyl(C₁-C₈)alkyl, it being possible for a phenylring to be substituted by F, Cl, Br, NO₂, CN, OCH₃, (C₁-C₄)alkyl orCH₃SO₂—; or is (C₁-C₄)alkoxy-(C₁-C₈)alkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl or two radicals R⁴⁹ together are (C₄-C₅)alkylene, itbeing possible for one CH₂ group to be replaced by O or S or for one ortwo CH₂ groups to be replaced by —NR^(d)—; R^(d) is H or (C₁-C₄)alkyl;m″ is 0 or 1; and p is 0, 1 or 2, inclusive of the stereoisomers and ofthe salts conventionally used in agriculture.
 2. A herbicidalcomposition as claimed in claim 1, which comprises a compound of theformula (I) where the symbols and indices have the following meanings: Ris hydrogen, (C₁-C₄)alkoxycarbonyl; R¹ is (C₃-C₇)cycloalkyl,(C₁-C₄)alkyl-(C₃-C₇)cycloalkyl; R² is hydrogen; R³ is hydrogen,(C₁-C₄)alkyl, arylsulfonyl, benzyl; R⁴ is (C₁-C₄)alkyl; R⁵ is(C₁-C₄)alkyl, (C₁-C₄)alkoxy; R⁶ is hydroxyl, (C₁-C₄)alkoxy; R⁷ is(C₃-C₇)cycloalkyl; R⁸ is cyano; m is an integer from 0 to 6, and Z is aradical selected from the group consisting of (Z1) to (Z4),

 where the symbols and indices have the following meanings: R⁹ is(C₁-C₄)alkyl, halogen, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkoxycarbonyl; R¹⁰ is benzyl,triazolylmethyl, pyrazolylmethyl, thiazolylmethyl,di-(C₁-C₄)alkylphosphono(C₁-C₄)alkyl; R¹¹ is (C₁-C₄)alkyl; R¹² is(C₁-C₄)alkyl, halogen, (C₁-C₄)haloalkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkoxycarbonyl; q is 0, 1, 2, 3 or 4; r is 0, 1, 2 or 3; t is 1or 2; u is 0, 1 or 2; v is 1 or 2; X¹ is O, CR¹⁴R¹⁵, CHOH, C═O,C═NO(C₁-C₄)alkyl; X² is SO₂; U¹ together with the linked carbon atomsforms a pyrazole, imidazole, pyrrole, pyridine, pyrimidine, thiazole,thienyl, oxazole or furan ring; U² is SO₂; R¹³ is hydrogen,(C₁-C₄)alkyl, (C₃-C₇)cycloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,optionally substituted phenyl, optionally substituted benzyl,(C₁-C₄)acyl; R¹⁴, R¹⁵ is identical or different hydrogen, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthioor R¹⁴ and R¹⁵ together form one of the groups —O—(CH₂)₂—O—,—O—(CH₂)₃—O—, S—(CH₂)₂—S—, —S—(CH₂)₃—S—, —(CH₂)₄—, —(CH₂)₅—; R²³ is(C₁-C₂)alkyl, Y¹, Y² are SO₂ or CO, with the proviso that Y¹≠Y².
 3. Aherbicidal composition as claimed in claim 1, wherein W in the formula(II) is a radical selected from the group consisting of (W1) to (W4),

where the symbols and indices have the following meanings: m′ is 0 or 1;R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₁₂)cycloalkyl ortri(C₁-C₄)alkylsilyl; R²⁷, R²⁸, R²⁹ are identical or different hydrogen,(C₁-C₈)alkyl, (C₁-C₈)haloalkyl, (C₃-C₁₂)cycloalkyl or substituted orunsubstituted phenyl.
 4. A herbicidal composition as claimed in claim 1comprising safeners of the formula (II) and/or (III) in which thesymbols and indices have the following meanings: R¹⁸, R²⁰ is —O—R²⁴; R²⁴is hydrogen, (C₁-C₁₈)alkyl, (C₃-C₁₂)cycloalkyl, (C₂-C₈)alkenyl and(C₂-C₁₈)alkynyl, it being possible for the carbon-containing groups tobe substituted by one or more radicals R⁵⁰; R⁵⁰ is identical ordifferent halogen, hydroxyl, (C₁-C₈)alkoxy, (C₁-C₈)alkylthio,(C₂-C₈)alkenylthio, (C₂-C₈)alkynylthio, (C₂-C₈)alkenyloxy,(C₂-C₈)alkynyloxy, (C₃-C₇)cycloalkyl, (C₃-C₇)cycloalkoxy, cyano, mono-and di(C₁-C₄)alkyl)amino, carboxyl, (C₁-C₈)alkoxycarbonyl,(C₂-C₈)alkenyloxycarbonyl, (C₁-C₈)alkylthiocarbonyl,(C₂-C₈)alkynyloxycarbonyl, (C₁-C₈)alkylcarbonyl, (C₂-C₈)alkenylcarbonyl,(C₂-C₈)alkynylcarbonyl, 1-(hydroxyimino)(C₁-C₆)alkyl,1-[(C₁-C₄)alkylimino](C₁-C₄)alkyl, 1-[(C₁-C₄)alkoxyimino](C₁-C₆)alkyl,(C₁-C₈)alkylcarbonylamino, (C₂-C₈)alkenylcarbonylamino,(C₂-C₈)alkynylcarbonylamino, aminocarbonyl, (C₁-C₈)alkylaminocarbonyl,di(C₁-C₆)alkylaminocarbonyl, (C₂-C₆)alkenylaminocarbonyl,(C₂-C₆)alkynylaminocarbonyl, (CD₁-C₈)alkoxycarbonylamino,(C₁-C₈)alkylaminocarbonylamino, (C₁-C₆)alkylcarbonyloxy, which isunsubstituted or substituted by R⁵¹, (C₂-C₆)alkenylcarbonyloxy,(C₂-C₆)alkynylcarbonyloxy, (C₁-C₈)alkylsulfonyl, phenyl,phenyl(C₁-C₆)alkoxy, phenyl(C₁-C₆)alkoxycarbonyl, phenoxy,phenoxy(C₁-C₆)alkoxy, phenoxy(C₁-C₆)alkoxycarbonyl, phenylcarbonyloxy,phenylcarbonylamino, phenyl(C₁-C₆)-alkylcarbonylamino, it being possiblefor the last-mentioned 9 radicals to be unsubstituted or mono- orpolysubstituted in the phenyl ring, by radicals R⁵²; SiR′₃, —O—SiR′₃,R′₃Si—(C₁-C₈)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂, —NR′₂,CH(OR′)₂, —O—(CH₂ _(m)—CH(OR′)₂, —CR′″(OR′)₂, —O—(CH₂)_(m)CR′″(OR″)₂ orby R″O—CHR′″CHCOR″—(C₁-C₆)—alkoxy, R⁵¹ is identical or differenthalogen, nitro, (C₁-C₄)alkoxy and phenyl which is unsubstituted orsubstituted by one or more radicals R⁵²; R⁵² is identical or differenthalogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy or nitro; R′ is identical or different hydrogen,(C₁-C₄)alkyl, phenyl which is unsubstituted or substituted by one ormore radicals R⁵², or two radicals R′ together form a (C₂-C₆)alkanediylchain; R″ is identical or different (C₁-C₄)alkyl or two radicals R″together form a (C₂-C₆)alkanediyl chain; R′″ is hydrogen or(C₁-C₄)alkyl; m is 0, 1, 2, 3, 4, 5 or
 6. 5. A herbicidal composition asclaimed in claim 1 comprising safeners of the formula (II) and/or (III)in which the symbols and indices have the following meanings: R²⁴ ishydrogen, (C₁-C₈)alkyl or (C₃-C₇)cycloalkyl, the abovementionedcarbon-containing radicals being unsubstituted or mono- orpolysubstituted by halogen or mono- or disubstituted by radicals R⁵⁰,R⁵⁰ is identical or different hydroxyl, (C₁-C₄)alkoxy, carboxyl,(C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₂-C₆)alkynyloxycarbonyl, 1-(hydroxyimino)(C₁-C₄)alkyl,1-[(C₁-C₄)alkylimino](C₁-C₄)alkyl and1-[(C₁-C₄)alkoxyimino](C₁-C₄)alkyl; —SiR′₃, —O—N═CR40 ₂, —N═CR′₂, —NR′₂and —O—NR′₂, in which R′ is identical or different hydrogen,(C₁-C₄)alkyl or, as a pair, a (C₄-C₅)alkanediyl chain, R²⁷, R²⁸, R²⁹ areidentical or different hydrogen, (C₁-C₈)alkyl, (C₁-C₆)haloalkyl,(C₃-C₇)cycloalkyl or phenyl which is unsubstituted or substituted by oneor more radicals selected from the group consisting of halogen, cyano,nitro, amino, mono- and di[(C₁-C₄)alkyl]amino, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio and(C₁-C₄)alkylsulfonyl; R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy)(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₇)cycloalkyl ortri(C₁-C₄)alkylsilyl, R¹⁷, R¹⁹ are identical or different hydrogen,halogen, methyl, ethyl, methoxy, ethoxy, (C₁ or C₂)haloalkyl.
 6. Aherbicidal composition as claimed in claim 1, comprising a safener ofthe formula (II) where the symbols and indices have the followingmeanings: R¹⁷ is hydrogen, halogen, nitro or (C₁-C₄)haloalkyl; n is 1, 2or 3; R¹⁸ is a radical of the formula OR²⁴, R²⁴ is hydrogen,(C₁-C₈)alkyl or (C₃-C₇)cycloalkyl, the abovementioned carbon-containingradicals being unsubstituted or mono- or polysubstituted by identical ordifferent halogen radicals or up to disubstituted by identical ordifferent radicals selected from the group consisting of hydroxyl,(C₁-C₄)alkoxy, (C₁-C₄)alkoxycarbonyl, (C₂-C₆)alkenyloxycarbonyl,(C₂-C₆)alkynyloxycarbonyl, 1-(hydroxyimino)(C₁-C₄)alkyl,1-[(C₁-C₄)alkylimino](C₁-C₄)alkyl, 1-[(C₁-C₄)alkoxyimino](C₁-C₄)alkyland radicals of the formulae —SiR′₃, —O—N═R′₂, —N═CR′₂, —NR′₂ and—O—NR′₂, the radicals R′ in the abovementioned formulae being identicalor different hydrogen, (C₁-C₄)alkyl or, in pairs, (C₄ or C₅)alkanediyl;R²⁷, R²⁸, R²⁹ are identical or different hydrogen, (C₁-C₈)alkyl,(C₁-C₆)haloalkyl, (C₃-C₇)cycloalkyl or phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, nitro, (C₁-C₄)haloalkyl and(C₁-C₄)haloalkoxy, and R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₇)cycloalkyl ortri(C₁-C₄)alkylsilyl.
 7. A herbicidal composition as claimed in one ormore of claims 1 to 6, wherein the weight ratio herbicide:safener is1:100 to 100:1.
 8. A herbicidal composition as claimed in one or more ofclaims 1 to 7, which comprises a further herbicide.
 9. A herbicidalcomposition as claimed in claim 8, wherein the further herbicide is asulfonylurea.
 10. A method of controlling harmful plants in crops, whichcomprises applying a herbicidally effective amount of aherbicide/safener combination as claimed in one or more of claims 1 to 8to the harmful plants, the plants, the seeds of the plants or the areaon which the plants grow.
 11. The method as claimed in claim 9, whereinthe plants are selected from the group consisting of maize, wheat, rye,barley, oats, rice, sorghum, cotton and soya.
 12. A method as claimed inclaim 10 or 11, wherein the plants are genetically engineered.